MARCEL DEKKER, INC. • 270 MADISON AVENUE • NEW YORK, NY 10016
©2003 Marcel Dekker, Inc. All rights reserved. This material may not be used or reproduced in any form without the express written permission of Marcel Dekker, Inc.
4-Nitrophenethylamine Hydrochloride
1831
Melting points are uncorrected. Elemental analysis was performed on a
Perkin–Elmer analyzer. The purity of the final product was checked using
an Agilent 1100 HPLC system. A reverse phase C18 Hypersil BDS
250 ꢀ 4.6 mm 5 m column was used. A solvent system containing 85% acet-
onitrile and 15% phosphate buffer with pH adjusted to 2.5 was employed
at flow rateof 1.0 mL/min [ ꢀ ¼ 280 nm].
4-Nitrophenyl-L-alanine Monohydrate 2: The Bergel and Stock[5]
procedure was used except that the crude product obtained was recrystal-
lized from water to give a yield of 47%.
4-Nitrophenethylamine HCl 3: To a suspension of 2 (5.0 g, 23.81 mM)
in 50 mL of diphenylether was added methyl ethyl ketone (MEK) 0.17 g
(2.37 mM). This was heated at 220ꢁC for 3 h resulting in a clear dark red
solution. This solution was diluted with 50 mL of diethyl ether and cooled
in ice bath. HCl gas was bubbled through the solution to obtain a dark red
precipitate which was filtered off. This residue was stirred in EtOAc and
filtered to obtain the desired product 3 as a brown solid with a yield of
3.75 g (78%), m.p. 200ꢁC decomp. IR (KBr): 2956, 2911, 1623, 1608, 1598,
1524, 1345, 1250, 1108, 856, 746 cmꢂ1. NMR (d-6, DMSO): ꢁ 3.07 (4H, br
s), 7.56 (2H, d, J ¼ 8.4 Hz), 8.18 (2H, d, J ¼ 8.4 Hz), 8.17–8.19 (3H,
embedded peaks). Anal. calcd. for C8H10N2O2 ꢃ HCl: C, 47.42; H, 5.47;
N, 13.82. Found: C, 47.45; H, 5.59; N, 13.48. HPLC purity>99%.
ACKNOWLEDGMENTS
Theauthors thank Dr. B. Gopalan, Dr. C. V. Srinivasan for helpful
discussions, and Dr. M. A. Khan for analytical support.
REFERENCES
1. Umino, N.; Iwakuma, T.; Itoh, N. Sodium acyloxyborohydrideas
new reducing agents. II. reduction of nitriles to the corresponding
amines. Tetrahedron Lett. 1976, 33, 2875–2876.
2. Suzuki, S.; Imai, Z.; Suzuki, Y.; Sato, T.; Miyaji, Y. Ger. Offen. 1970,
GWXXBX DE 2008443 19700224.
3. Mash, L.I.; Gerasimova, N.E. USSR Patent, URXXAF SU 620476
1,978,0825, 1978.
4. Johnson, T.B.; Guest, H.H. Synthesis of 4-nitrophenyl ethyl amine
and 2,4 dinitrophenyl ethyl amine. Am. Chem. J. 1910, 43, 310–
322.