Water → 2-Phenoxypyridine-3-carboxylic acid (3-trifluoromethylbenzylidene)-hydrazide

HRID 2084260Notes

Reaction equation

HRID 2084260 reaction equation
[O:1]([C:8]1[C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]([F:29])([F:28])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=O.O>C(O)C>[F:18][C:19]([F:28])([F:29])[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH:23]=[N:17][NH:16][C:14]([C:13]1[C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 679903-(Trifluoromethyl)benzaldehydeHCID 27976852-Phenoxynicotinohydrazide

Product 1

HCID 865871582-Phenoxypyridine-3-carboxylic acid (3-trifluoromethylbenzylidene)-hydrazideYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-phenoxypyridine-3-carboxylic acid hydrazide (913 mg, 4 mmol), 3-trifluoromethylbenzaldehyde (696 mg, 4 mmol) in ethanol (40 mL) was refluxed for 13 h. It was cooled to room temperature and some precipitate was observed. The mixture was diluted by water (40 mL) and the solid was collected by filtration and washed with ethanol/water (1:1), dried to give 1.41 g (92%) of the title compound. 1H NMR (CDCl3): 10.84 (s, 1H), 8.63 (m, 1H), 8.23 (s, 1H), 8.16 (m, 1H), 7.91 (bs, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.54 (d, J=7.8 Hz, 1H), 7.40 (m, 3H), 7.24 (t, J=7.2 Hz, 1H), 7.18-7.08 (m, 3H).

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with ethanol/water (1:1)
  3. customdried

Sources & evidence

ORD record
ord-c2d29f66f5044edd8c8f29a13794f455
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Reaction notes

Loading…