Water → HCID 178519561, compound

HRID 275259Notes

Reaction equation

HRID 275259 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].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([Cl:33])[C:24]=1[NH:34][NH2:35].O>C1(C)C=CC=CC=1>[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:31])([F:30])[F:32])[CH:26]=[C:25]([Cl:33])[C:24]=1[NH:34][N:35]=[C:10]([OH:12])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:21])[F:20])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 200788952-(3-Trifluoromethylbenzoyl)nicotinic acid

Product 1

HCID 178519561HCID 178519561, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 2-(3-trifluoromethylbenzoyl)nicotinic acid (1.5 g) and 2,6-dichloro-4-trifluoromethylphenylhydrazine (1.87 g) in toluene was stirred at reflux with azeotropic removal of water (using a Dean Stark apparatus) for 6.5 hours. The mixture was cooled to room temperature and then washed with 2N hydrochloric acid and water. The organic phase was dried and evaporated. The crude product was purified by column chromatography to yield a yellow gum which was triturated in hexane to yield the title compound as a pale yellow solid (0.24 g), m.p. 92°-96° C.

Workup

  1. customfor 6.5 hours
  2. washwashed with 2N hydrochloric acid and water
  3. customThe organic phase was dried
  4. customevaporated
  5. customThe crude product was purified by column chromatography
  6. customto yield a yellow gum which
  7. customwas triturated in hexane

Sources & evidence

ORD record
ord-274805c1a99948e788ffde0c216112e5
Source dataset
uspto-grants-1995_02
Patent number
US05393730

Reaction notes

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