Table 2. Physical and analytical data of 20-hydroxychalcones
Compd
Melting point (ꢀC)a
Yield (%)
Elemental analysis
C, H,
Accurate mass (M+1)
1H NMR (d ppm)
292.0067
(C15H10O2Cl2=292.0058)
In DMSO, 12.65 (s, OH) 8.26 (s, J=15.44 Hz, bH) 7.62 (s, J=15.44 Hz, aH)
7.88–6.95 (m, 20H, 30H, 50H, 60H, 3H, 5H, 6H)
231
232
176–178
69–71
10.0
25.0
Cl: calcd 23.95, found 24.33
C, H,
267.1251
(C17H17O2N=267.1259)
In DMSO, 12.72 (s, OH) 7.95 (s, J=15.07 Hz, bH) 7.59 (s, J=15.07 Hz, aH)
7.95–6.68 (m, 20H, 30H, 50H, 60H, 2H, 3H, 5H, 6H) 3.03 (s, –N–(CH3)2)
N: calcd 5.24, found 5.39
C, H,
233
196–198
32.6
275.0938
(C18H13O2N=275.0946)
In DMSO, 12.42 (s, OH), 9.20 (d, 2H) 8.26 (s, J=15.83 Hz, bH), 7.53
(s, J=15.82 Hz, aH), 8.30–6.82 (m, 4H, 5H, 6H, 7H, 8H, 20H, 30H, 50H, 60H)
N: calcd 5.09, found 5.18
C: calcd 69.76, found 70.04
258.0443
(C15H11O2Cl=258.0447)
In DMSO, 12.77 (s, OH), 7.84 (m, J=15.83 Hz, bH), 7.61 (m, J=15.45 Hz,
aH), 7.89–6.94 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H)
234
235
149–150
48.1
44.6
H: calcd 4.30, found 4.75
Cl: calcd 13.55, found 13.28
C, H
114–115
120–121b
238.0986
(C16H14O2=238.0994)
In DMSO, 12.88 (s, OH), 7.91 (s, J=15.45 Hz, bH), 7.62 (d, J=15.45 Hz,
aH), 7.92–6.94 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H), 2.36 (s, CH3)
236
89–91
91–92b
35.4
C, H
C,
254.0946
(C16H14O3=254.0943)
In DMSO, 12.95 (s, OH), 7.90 (s, J=15.45 Hz, bH), 7.54 (s, J=15.45 Hz,
aH), 7.92–6.95 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H), 3.82 (s, OCH3)
284.1049
(C17H16O4=284.1049)
In DMSO, 12.90 (s, OH), 7.96 (d, J=15.8 Hz, bH), 7.65 (d, J=15 Hz, aH),
7.98–6.57 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H), 3.90 (s, OCH3), 3.82
(s, OCH3)
237
238
111–113
25.0
46.4
H: calcd 5.68, found 5.47
C: calcd 65.74, found 64.95
292.0704
(C16H11O2F3=292.0711)
In DMSO, 12.69 (s, OH), 8.03 (m, J=15.82 Hz, bH), 7.70 (m, J=15.45 Hz,
aH), 8.11–6.90 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H)
<50
H: calcd 3.80, found 3.78
F: calcd 19.51, found 19.71
C,
242.0732
(C15H11O2F=242.0743)
In DMSO, 12.37 (s, OH), 7.88 (m, J=15.45 Hz, bH), 7.64 (d, J=15.45 Hz,
aH), 8.08–6.88 (m, 2H, 3H, 5H, 6H, 20H, 30H, 50H, 60H)
239
<50
43.5
H: calcd 4.58, found 4.50
F: calcd 7.85, found 7.62
C,
225.0785
(C14H11O2N=225.0790)
In DMSO, 12.73 (s, OH), 8.43–8.38 (d, J=15.45 Hz, bH), 7.77–7.72
(d, J=15.45 Hz, aH), 8.82–6.93 (m, 3H, 4H, 5H, 6H, 20H, 30H, 50H, 60H)
241
242
89–91
25.3
41.1
H: calcd 4.93, found 5.03
N: calcd 6.22, found 6.38
C, H
106–108
274.0993
In DMSO, 12.42 (s, OH), 8.69 (d, J=15.45 Hz, bH), 7.73 (d, J=15.44 Hz,
aH) 8.50–6.70 (m, 2H, 3H, 4H, 5H, 6H, 7H, 8H, 20H, 30H, 50H, 60H)
In DMSO, 12.16 (s, OH), 8.07–8.02 (d, J=15.44 Hz, bH), 7.76–7.71 (d, J=
15.45 Hz, aH) 8.40–6.83 (m, 1H, 3H, 4H, 5H, 6H, 7H, 8H, 20H, 30H, 50H,
60H)
(C19H14O2=274.0994)
274.1003
(C19H14O2=274.0994)
C,
243
244
146–148
151–153
39.6
11.2
H: calcd 5.15, found 5.10
C,
275.0960
(C18H13O2N=275.0946)
In DMSO, 12.39 (s, OH), 8.48–8.43(d, J=15.45 Hz, bH), 8.37–8.31 (d, J=
15.45 Hz, aH), 9.27–6.93 (m, 2H, 3H, 5H, 6H, 7H, 8H, 20H, 30H, 50H, 60H)
H: calcd 4.76, found 4.89
N: calcd 5.09, found 5.21
aRecrystallized from methanol.
bCited in product catalog (2000/2001) of Indofine Chemical Company, Inc. (Somerville, NJ, USA).