Water → Biphenyl-2-carboxylic acid (3-trifluoromethyl-benzylidene)-hydrazide

HRID 1791388Notes

Reaction equation

HRID 1791388 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]([C:7]([NH:9][NH2:10])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[F:17][C:18]([F:28])([F:27])[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.O>CCO>[F:17][C:18]([F:27])([F:28])[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[N:10][NH:9][C:7]([C:2]1[C:1]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 679903-(Trifluoromethyl)benzaldehydeHCID 27603652-Phenylbenzhydrazide

Product 1

HCID 86587161Biphenyl-2-carboxylic acid (3-trifluoromethyl-benzylidene)-hydrazideYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of biphenyl-2-carboxylic acid-hydrazide (0.212 g, 1.0 mmol) in 20 mL EtOH was added 3-trifluoromethyl-benzaldehyde (0.174 g, 1.0 mmol) in 5 mL EtOH at room temperature. The mixture was refluxed for 4 h and cooled to room temperature, then was diluted by 100 mL of water. The precipitate was collected, washed with MeOH, and dried to yield the title compound (0.320 g, 87%). 1H NMR (acetone-d6): 11.60 (s, 1H), 7.79 (s, 1H), 7.57 (s, 1H), 7.52 (d, J=12 Hz, 1H), 7.35 (d, J=12 Hz, 1H), 6.97˜7.15 (m, 10H).

Workup

  1. temperatureThe mixture was refluxed for 4 h
  2. customThe precipitate was collected
  3. washwashed with MeOH
  4. customdried

Sources & evidence

ORD record
ord-47adc2ac387f4000a9d9c47a18468d30
Source dataset
uspto-grants-2006_07
Patent number
US07074813B2

Reaction notes

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