2-Fluoro-4-(trifluoromethyl)aniline → 6-Chloro-N-(2-fluoro-4-trifluoromethyl-phenyl)-nicotinamide

HRID 2190526Notes

Reaction equation

HRID 2190526 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][N:15]=1.ClC1C=CC(C(NC2C=CC(I)=C(C)C=2)=O)=CN=1>>[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:4][C:3]2[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:2]=2[F:1])=[O:19])=[CH:16][N:15]=1

Participants

4

Reactant 3

HCID 27376742-Fluoro-4-(trifluoromethyl)anilineHCID 27821656-Chloronicotinoyl ChlorideHCID 593181386-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide

Product 1

HCID 593180766-Chloro-N-(2-fluoro-4-trifluoromethyl-phenyl)-nicotinamide

Procedure

6-Chloro-N-(2-fluoro-4-trifluoromethyl-phenyl)-nicotinamide was prepared from 2-fluoro-4-trifluoromethyl aniline and 6-chloronicotinoyl chloride following a procedure similar to the one described in the synthesis of 6-chloro-N-(4-iodo-3-methyl-phenyl)-nicotinamide, above. The product was isolated after precipitation out of a small volume of CH2Cl2 with hexanes. HRMS m/z calcd for C13H7N2OClF4 [M+H]+: 319.0256. Found: 319.0255.

Workup

  1. customThe product was isolated
  2. customafter precipitation out of a small volume of CH2Cl2 with hexanes

Sources & evidence

ORD record
ord-edfa1a8f7b2a4ca9a94fe4cf1eb271ef
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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