2-(3-methoxyphenyl)acetohydrazide

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-[(4-methylphenyl)sulfonyl]benzaldehyde (500 mg, 1.92 mmol) in EtOH (10 mL) is added 2-(3-methoxyphenyl)acetohydrazide (329 mg, 1.92 mmol) and the reaction is heated to 80° C. for 1 h. While cooling a white precipitate forms, and this solid is isolated by filtration and washed with portions of EtOH and Et2O. This solid was dried under vacuum to provide 2-(3-methoxyphenyl)-N′-((1E)-{2-[(4-methylphenyl)sulfonyl]phenyl}methylene)acetohydrazide (313 mg, 39%). 1H-NMR (400 MHz, DMSO-d6) 12.00–11.85 (m, 1H), 8.95–8.80 (m, 1H), 8.16–8.10 (m, 1H), 7.99–7.81 (2H), 7.72–7.65 (m, 2H), 7.42–7.37 (m, 2H), 7.27–7.16 (m, 1H), 6.93–6.76 (m, 4H), 3.92–3.36 (m, 5H), 2.35 (s, 3H). ESI+ for C23H22N2O4S, m/z: 423, (M+H)+. While cooling a white precipitate forms this solid is isolated by filtration washed with portions of EtOH and Et2O This solid was dried under vacuum

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in a similar manner to that described in example 1 from of 8-hydroxy-1,6-naphthyridine-7-carbonitrile (50 mg, 0.29 mmol) and 2-(3-methoxyphenyl)acetic hydrazide (270 mg, 1.5 mmol) as a yellow solid (20 mg, 21%). 1H NMR (CDCl3): δ 9.19 (m, 1 H), 8.91 (s, 1 H), 8.31 (d, J=7.6 Hz, 1 H), 7.63 (m, 1 H), 7.22 (m, 1 H), 7.01-6.97 (m, 2 H), 6.83-6.79 (m, 2 H), 4.23 (s, 2 H), 3.79 (s, 3 H); MS m/z 334 (M+1).