2-Phenoxypyridine-3-carbonyl chloride → N'-(2-phenoxypyridine-3-carbonyl)-3-(trifluoromethyl)benzhydrazide

HRID 2084259

Reaction equation

HRID 2084259 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([NH:8][NH2:9])=[O:7].[O:15]([C:22]1[C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>N1C=CC=CC=1>[O:15]([C:22]1[C:27]([C:28]([NH:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][CH:12]=[C:3]([C:2]([F:13])([F:14])[F:1])[CH:4]=2)=[O:29])=[CH:26][CH:25]=[CH:24][N:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 27743062-Phenoxypyridine-3-carbonyl chlorideHCID 27774173-(Trifluoromethyl)benzoic acid hydrazide

Product 1

HCID 2797700N'-(2-phenoxypyridine-3-carbonyl)-3-(trifluoromethyl)benzhydrazideYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 3-(trifluoromethyl)benzhydrazide (102.1 mg, 0.5 mmol), 2-phenoxypyridine-3-carbonyl chloride (117 mg, 0.5 mmol) in pyridine (5 mL) was refluxed for 2 h. It was evaporated in vacuo and the residue was purified by column chromatography (silica gel, EtOAc/CH2Cl2=4:1) to give 107 mg (54%) of the title compound. 1H NMR (CDCl3): 10.88 (d, J=6.3 Hz, 1H), 9.80 (d, J=6.3 Hz, 1H), 8.60 (m, 1H), 8.30 (m, 1H), 8.17 (s, 1H), 8.06 (d, J=8.1 Hz, 1H), 7.81 (d, J=7.8 Hz, 1H), 7.61 (t, J=7.2 Hz, 1H), 7.51-7.46 (m, 2H), 7.34-7.17 (m, 4H).

Workup

  1. customIt was evaporated in vacuo
  2. customthe residue was purified by column chromatography (silica gel, EtOAc/CH2Cl2=4:1)

Sources & evidence

ORD record
ord-2e7aeacbf3764d5d8b8f5e4f1e8c04e6
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Linked notes

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