(R)-N-[3-nitro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide → (R)-N-[3-Amino-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

HRID 2120361Notes

Reaction equation

HRID 2120361 reaction equation
[N+:1]([C:4]1[C:5]([Cl:20])=[C:6]([NH:10][C:11](=[O:19])[C@:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[C:5]([Cl:20])=[C:6]([NH:10][C:11](=[O:19])[C@:12]([OH:18])([CH3:17])[C:13]([F:14])([F:15])[F:16])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 58964771(R)-N-[3-nitro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide

Product 1

HCID 58964770(R)-N-[3-Amino-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamideYield 100.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (R)-N-[3-nitro-2-chlorophenyl]-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 3) (14.3 g) in EtOAc (250 ml) under a hydrogen atmosphere was added 10% palladium on carbon (1.6 g). The reaction mixture was allowed to stir at room temperature overnight; the mixture was filtered through a pad of diatomaceous earth and volatile material was removed by evaporation to give the title compound (13 g) as a brown solid. NMR (CDCl3) 1.75 (s, 3H), 4.00 (s, 1H), 4.10 (brs, 2H), 6.61 (d, 1H), 7.08 (t, 1H), 7.72 (d, 1H), 8.77 (brs, 1H); m/z: 281.

Workup

  1. filtrationthe mixture was filtered through a pad of diatomaceous earth and volatile material
  2. customwas removed by evaporation

Sources & evidence

ORD record
ord-c1a0495d85154f759656a5dcbc2fcd86
Source dataset
uspto-grants-2004_02
Patent number
US06689909B1

Reaction notes

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