4-(Trifluoromethyl)phenylhydrazine → 2-(3-Trifluoromethylbenzoyl)nicotinic acid (4-trifluoromethylphenyl)hydrazone

HRID 275258

Reaction equation

HRID 275258 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O)=[O:7].[F:22][C:23]([F:33])([F:32])[C:24]1[CH:29]=[CH:28][C:27]([NH:30][NH2:31])=[CH:26][CH:25]=1>CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:22][C:23]([F:32])([F:33])[C:24]1[CH:25]=[CH:26][C:27]([NH:30][N:31]=[C:10]([OH:12])[C:9]2[CH:13]=[CH:14][CH:15]=[N:16][C:8]=2[C:6](=[O:7])[C:5]2[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:21])[F:20])[CH:4]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 1362004-(Trifluoromethyl)phenylhydrazineHCID 200788952-(3-Trifluoromethylbenzoyl)nicotinic acid

Product 1

HCID 1785195602-(3-Trifluoromethylbenzoyl)nicotinic acid (4-trifluoromethylphenyl)hydrazoneYield 80.7%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 887MethanolSolvent

Procedure

2-(3-Trifluoromethylbenzoyl)nicotinic acid (0.5 g), 4-trifluoromethylphenylhydrazine (0.3 g) and para-toluene sulphonic acid (0.001 g) were stirred in methanol at room temperature for 22 hours. Solvent was evaporated. The residue was triturated in cold toluene then dried to yield the title compound as a beige solid (0.62 g), m.p. 127°-129° C.

Workup

  1. customSolvent was evaporated
  2. customThe residue was triturated in cold toluene
  3. customthen dried

Sources & evidence

ORD record
ord-0f21748979904a6cb9e4027cefd1fe85
Source dataset
uspto-grants-1995_02
Patent number
US05393730

Linked notes

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