Job/Unit: O42451
/KAP1
Date: 24-07-14 18:10:54
Pages: 10
W. Zhang, D. Wu, J. Zhang, Y. Liu
168 (15). HRMS (EI): m/z calcd. for C8H7ClN2O3 214.0145; found
FULL PAPER
= 148.0, 143.9, 136.1, 133.5, 129.7, 125.8, 124.9, 62.7 ppm. MS (EI,
70 eV): m/z (%) = 214 (38) [M+], 168 (21). HRMS (EI): m/z calcd. 214.0137.
for C8H7ClN2O3 214.0145; found 214.0150.
(E)-5-Bromo-2-nitrobenzaldehyde O-Methyl Oxime (2m): Yield
(E)-2-Nitro-4-(trifluoromethyl)benzaldehyde O-Methyl Oxime (2e):
60.6 mg (78%); white solid; m.p. 109–110 °C. IR (KBr): ν = 1515
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Yield 54.3 mg (73%); yellow oil. IR (neat): ν = 1502 (NO ) cm–1.
(NO2) cm–1. H NMR (CDCl3, 500 MHz): δ = 8.59 (s, 1 H), 8.16
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1H NMR (CDCl3, 500 MHz): δ = 8.63 (s, 1 H), 8.32 (s, 1 H), 8.19
(d, J = 2.0 Hz, 1 H), 7.94 (d, J = 8.5 Hz, 1 H), 7.66 (dd, J = 8.5,
(d, J = 8.5 Hz, 1 H), 7.88 (d, J = 8.5 Hz, 1 H), 4.07 (s, 3 H) ppm. 2.0 Hz, 1 H), 4.05 (s, 3 H) ppm. 13C NMR (CDCl3, 125 MHz): δ
13C NMR (125 MHz, CDCl3): δ = 147.5, 143.6, 132.3 (q, JF,C
33.8 Hz), 130.6, 129.6 (q, JF,C = 3.1 Hz), 129.55, 122.6 (q, JF,C
=
=
= 146.4, 143.8, 133.1, 131.4, 129.0, 128.5, 126.3, 62.8 ppm. MS (EI,
70 eV): m/z (%) = 258 (23) [M+], 212 (17). HRMS (EI): m/z calcd.
for C8H7BrN2O3 257.9640; found 257.9646.
250.0 Hz), 122.2 (q, JF,C = 4.2 Hz), 62.9 ppm. MS (EI, 70 eV): m/z
(%) = 248 (50) [M+], 202 (18). HRMS (EI): m/z calcd. for
C9H7F3N2O3 248.0409; found 248.0414.
(E)-2-Nitro-1-naphthaldehyde O-Methyl Oxime (2h): Yield 45.6 mg 1512 (NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.75 (s, 1 H),
(E)-5-(Naphthalen-2-yl)-2-nitrobenzaldehyde O-Methyl Oxime (2n):
Yield 50.5 mg (55%); yellow solid; m.p. 103–104 °C. IR (KBr): ν =
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1
(66%); yellow solid; m.p. 74–75 °C. IR (KBr): 1519 8.30 (d, J = 2.0 Hz, 1 H), 8.20 (d, J = 8.5 Hz, 1 H), 8.13 (d, J =
ν
=
˜
(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.72 (s, 1 H), 8.49–
8.47 (m, 1 H), 8.08–7.99 (m, 2 H), 7.96–7.94 (m, 1 H), 7.72–7.70
(m, 2 H), 4.08 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ =
146.4, 144.5, 135.3, 131.3, 130.7, 129.3, 128.6, 128.4, 127.7, 125.1,
1.0 Hz, 1 H), 7.99–7.90 (m, 3 H), 7.85 (dd, J = 8.5, 2.0 Hz, 1 H),
7.77 (dd, J = 8.5, 2.0 Hz, 1 H), 7.58–7.56 (m, 2 H), 4.09 (s, 3
H) ppm. 13C NMR (125 MHz, CDCl3): δ = 146.52, 146.48, 145.4,
135.6, 133.5, 133.3, 129.0, 128.7, 128.5, 128.0, 127.8, 127.4, 127.0,
1
120.1, 62.5 ppm. MS (EI, 70 eV): m/z (%) = 230 (45) [M+], 184 126.9, 126.8, 125.7, 124.9, 62.6 ppm. MS (EI, 70 eV): m/z (%) =
(12). HRMS (EI) for C12H10N2O3: calcd. 230.0691, found
230.0684.
306 (38) [M+], 160 (21). HRMS (EI): m/z calcd. for C18H14N2O3
306.1004; found 306.1014.
(E)-3-Nitro-2-naphthaldehyde O-Methyl Oxime (2i): Yield 27.6 mg (E)-4-Nitro-[1,1Ј-biphenyl]-3-carbaldehyde O-Methyl Oxime (2o):
(40%); yellow solid; m.p. 120–121 °C. IR (KBr): ν = 1542 Yield 61.5 mg (80%). IR (neat): ν = 1517 (NO ) cm–1. 1H NMR
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1
(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.70 (s, 1 H), 8.65
(500 MHz, CDCl3): δ = 8.72 (s, 1 H), 8.17 (dd, J = 7.5, 2.0 Hz, 1
H), 7.73 (dd, J = 8.5, 2.0 Hz, 1 H), 7.68–7.66 (m, 2 H), 7.53–7.46
(s, 1 H), 8.37 (s, 1 H), 7.99 (t, J = 7.0 Hz, 2 H), 7.73–7.65 (m, 2
H), 4.08 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 145.8, (m, 3 H), 4.06 (s, 3 H) ppm. 13C NMR (126 MHz, CDCl3): δ =
145.3, 134.8, 132.2, 130.1, 129.4, 129.3, 128.7, 128.5, 125.9, 123.4,
146.6, 146.5, 145.3, 138.4, 129.2, 129.0, 128.5, 127.9, 127.4, 127.2,
62.4 ppm. MS (EI, 70 eV): m/z (%) = 230 (83) [M+], 184 (12).
125.6, 62.5 ppm. MS (EI, 70 eV): m/z (%) = 256 (21) [M+], 208 (38).
HRMS (EI): m/z calcd. for C12H10N2O3 230.0691; found 230.0686. HRMS (EI): m/z calcd. for C14H12N2O3 256.0848; found 256.0839.
(E)-1-Nitro-2-naphthaldehyde O-Methyl Oxime (2iЈ): Yield 26.2 mg (E)-3Ј-Methyl-4-nitro-[1,1Ј-biphenyl]-3-carbaldehyde O-Methyl Ox-
(38%); yellow solid; m.p. 86–87 °C. IR (KBr):
ν = 1518 ime (2p): Yield 50.3 mg (62%); yellow oil. IR (neat): ν = 1519
˜ ˜
1
1
(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.38 (s, 1 H), 8.07
(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.71 (s, 1 H), 8.16–
(dd, J = 8.5, 1.0 Hz, 1 H), 7.97 (dd, J = 8.0, 1.0 Hz, 1 H), 7.93 (dd,
8.14 (m, 2 H), 7.72 (dd, J = 8.5, 2.0 Hz, 1 H), 7.46–7.29 (m, 4 H),
J = 7.5, 1.5 Hz, 1 H), 7.79 (d, J = 7.0 Hz, 1 H), 7.63 (t, J = 8.0 Hz, 4.07 (s, 3 H), 2.47 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ
1 H), 7.55 (t, J = 8.0 Hz, 1 H), 3.97 (s, 3 H) ppm. 13C NMR
= 146.7, 146.4, 145.4, 138.9, 138.3, 129.8, 129.0, 128.5, 128.1, 127.9,
(125 MHz, CDCl3): δ = 148.3, 147.1, 135.1, 133.5, 130.4, 130.0, 127.2, 125.5, 124.5, 62.5, 21.5 ppm. MS (EI, 70 eV): m/z (%) = 270
127.3, 126.9, 124.8, 124.1, 122.0, 62.3 ppm. MS (EI, 70 eV): m/z (32) [M+], 224 (26). HRMS (EI): m/z calcd. for C15H14N2O3
(%) = 230 (10) [M+], 184 (60). HRMS (EI): m/z for C12H10N2O3 270.1004; found 270.1012.
230.0691; found 230.0682.
(E)-3Ј-Chloro-4-nitro-[1,1Ј-biphenyl]-3-carbaldehyde O-Methyl Ox-
(E)-5-Methyl-2-nitrobenzaldehyde O-Methyl Oxime (2j): Yield
ime (2q): Yield 66.3 mg (76%); yellow solid; m.p. 90–91 °C. IR
40.8 mg (70%); yellow solid; m.p. 51–52 °C. IR (KBr): ν = 1515 (KBr): ν = 1513 (NO ) cm–1. 1H NMR (500 MHz, CDCl3): δ =
˜
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2
1
(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.65 (s, 1 H), 8.00
(d, J = 8.5 Hz, 1 H), 7.76 (s, 1 H), 7.33 (d, J = 7.0 Hz, 1 H), 4.04
(s, 3 H), 2.48 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ =
145.5, 144.9, 130.8, 129.1, 127.3, 125.0, 62.4, 21.4 ppm. MS (EI,
8.69 (s, 1 H), 8.17–8.15 (m, 2 H), 7.70 (dd, J = 8.5, 2.0 Hz, 1 H),
7.64–7.63 (m, 1 H), 7.54–7.52 (m, 1 H), 7.45–7.44 (m, 2 H), 4.07
(s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 146.8, 144.99,
144.95, 140.1, 135.1, 130.4, 129.0, 128.5, 128.0, 127.5, 127.2, 125.7,
70 e V): m/z (%) = 194 (51) [M+], 148 (27). HRMS (EI): m/z calcd. 125.6, 62.6 ppm. MS (EI, 70 eV): m/z (%) = 290 (26) [M+], 244
for C9H10N2O3 194.0691; found 194.0686.
(19). HRMS (EI): m/z calcd. for C14H11ClN2O3 290.0458; found
290.0450.
(E)-5-Methoxy-2-nitrobenzaldehyde O-Methyl Oxime (2k): Yield
1.5 mg (50%); yellow solid; m.p. 69–70 °C. IR (KBr): ν = 1527
(E)-4Ј-Methyl-4-nitro-[1,1Ј-biphenyl]-3-carbaldehyde O-Methyl Ox-
ime (2r): Yield 55.9 mg (69%); yellow solid; m.p. 77–78 °C. IR
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(NO2) cm–1. H NMR (500 MHz, CDCl3): δ = 8.56 (s, 1 H), 7.92
(d, J = 9.0 Hz, 1 H), 7.53 (d, J = 2.5 Hz, 1 H), 7.17 (dd, J = 8.5, (KBr): ν = 1511 (NO ) cm–1. 1H NMR (500 MHz, CDCl3): δ =
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2
2.5 Hz, 1 H), 4.01 (s, 3 H), 3.91 (s, 3 H) ppm. 13C NMR (125 MHz, 8.71 (s, 1 H), 8.16–8.14 (m, 2 H), 7.72 (dd, J = 8.5, 2.0 Hz, 1 H),
CDCl3): δ = 160.8, 148.6, 144.8, 129.8, 120.3, 119.7, 109.0, 62.3,
56.0 ppm. MS (EI, 70 eV): m/z (%) = 210 (29) [M+], 164 (16).
HRMS (EI): m/z calcd. for C9H10N2O4 210.0641; found 210.0637.
7.57 (d, J = 8.0 Hz, 2 H), 7.32 (d, J = 8.0 Hz, 2 H), 4.06 (s, 3 H),
2.44 (s, 3 H) ppm. 13C NMR (125 MHz, CDCl3): δ = 146.5, 146.2,
145.4, 139.2, 135.4, 129.9, 128.2, 127.9, 127.2, 126.9, 125.6, 62.5,
21.2 ppm. MS (EI, 70 eV): m/z (%) = 270 (100) [M+], 224 (42).
HRMS (EI): m/z calcd. for C15H14N2O3 270.1004; found 270.1009.
(E)-5-Chloro-2-nitrobenzaldehyde O-Methyl Oxime (2l): Yield
51.5 mg (80%); white solid; m.p. 87–88 °C. IR (KBr): ν = 1516
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1
(NO2) cm–1. H NMR (CDCl3, 500 MHz): δ = 8.61 (s, 1 H), 8.04–
(E)-4Ј-Methoxy-4-nitro-[1,1Ј-biphenyl]-3-carbaldehyde
O-Methyl
8.00 (m, 2 H), 7.50 (dd, J = 9.0, 2.5 Hz, 1 H), 4.06 (s, 3 H) ppm.
Oxime (2s): Yield 52.4 mg (61%). IR (neat): ν = 1514 (NO ) cm–1.
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13C NMR (CDCl3, 125 MHz): δ = 145.9, 143.9, 140.1, 130.0, 129.1, 1H NMR (500 MHz, CDCl3): δ = 8.72 (s, 1 H), 8.15 (d, J = 8.5 Hz,
128.4, 126.4, 62.8 ppm. MS (EI, 70 eV): m/z (%) = 214 (24) [M+],
1 H), 8.13 (d, J = 8.5 Hz, 1 H),7.69 (dd, J = 9.0, 2.5 Hz, 1 H), 7.62
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