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

HRID 1894011Notes

Reaction equation

HRID 1894011 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]>[Pd].C1COCC1>[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 suspension of 5-acetyl-2-acetylamino-4-trifluoromethyl-benzoic acid methyl ester (1.0 g, 3.3 mmol) and 100 mg of palladium on carbon (10%) in THF (10 mL) was stirred at r.t. for 2 h under hydrogen (5 bars). The mixture was then filtered and concentrated in vacuo. The crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 2:1) to give 2-acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (917 mg, 3.0 mmol, 91%) as a white solid, m.p. 120-122° C., ESI-MS: m/z 306 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by column chromatography (silica gel 60, hexanes/EtOAc 2:1)

Sources & evidence

ORD record
ord-2d9bd0f464dc4d99aea9e19ca261388d
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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