5-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester → 2-Acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 1441537Notes

Reaction equation

HRID 1441537 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19]>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([OH:12])[CH3:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH:17][C:18](=[O:20])[CH3:19]

Participants

4

Reactant 1

HCID 591644065-Acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 591644842-Acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl esterYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (4 g, 13.2 mmol) in THF (40 mL) was hydrogenated at r.t. for 2 h over Pd—C (10%, 250 mg). The reaction mixture was filtered on a sintered funnel. The filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, 2:1 hexanes/EtOAc) to give the title product (3.66 g, 91% yield) as colorless crystals. m.p.: 120-123° C., ESI-MS: m/z 306 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered on a sintered funnel
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, 2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-8a7410534c3840ec8e7b8fc1b4da9e2a
Source dataset
uspto-grants-2010_02
Patent number
US07655666B2

Reaction notes

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