Acetamide, 2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]- → N-(3-aminobenzyl)-2,2,2-trifluoroacetamide

HRID 1157591Notes

Reaction equation

HRID 1157591 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)=[O:4].[H][H]>CC(O)C.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([CH2:6][NH:5][C:3](=[O:4])[C:2]([F:1])([F:16])[F:17])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 57842617Acetamide, 2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]-HCID 178418361HCID 178418361, compound

Product 1

HCID 21131928N-(3-aminobenzyl)-2,2,2-trifluoroacetamideYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-[(3-nitrophenyl)methyl]acetamide (0.5 g, 2.0 mmol) in i-PrOH was added 10% Pd/C (40 mg, 0.04 mmol). A balloon filled with hydrogen gas was installed, and the reaction was stirred vigorously at rt. After 15 h, the reaction mixture was filtered through celite, adsorbed onto silica gel, and purified by column chromatography to generate the title compound in 85% yield. 1H NMR (400 MHz, CDCl3) δ 7.14-7.27 (m, 1H), 6.59-6.68 (m, 3H), 4.43 (s, 2H), 3.74 (s, 2H). ES-LC/MS m/z=219 [M+H]+.

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. custompurified by column chromatography

Sources & evidence

ORD record
ord-367a1c602e6f481697ad3cb1e5e11120
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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