Ethyl Acetate → 2-Amino-5-(1-ethoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 1894014Notes

Reaction equation

HRID 1894014 reaction equation
[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(=O)C.O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1.CCOC(C)=O>CCO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([CH:10]([O:12][CH2:23][CH3:24])[CH3:11])[C:7]([C:13]([F:14])([F:15])[F:16])=[CH:6][C:5]=1[NH2:17]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 591644842-Acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 119653762-Amino-5-(1-ethoxy-ethyl)-4-trifluoromethyl-benzoic acid methyl esterYield 179%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-acetylamino-5-(1-hydroxy-ethyl)-4-trifluoromethyl-benzoic acid methyl ester (500 mg, 1.64 mmol) in EtOH (5 mL) was treated with p-toluenesulfonic acid monohydrate (100 mg, 0.518 mmol) and stirred at r.t. for 5 d. The reaction mixture was taken into EtOAc and washed with sat. aq NaHCO3. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc) to give title product (270 mg, 57%) as colorless crystals. m.p.: 100-103° C., API-ES: m/z 292 [M+H]+.

Workup

  1. washwashed with sat. aq NaHCO3
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (silica gel, 5:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-0ac56075d7de4959ae204a4172b43eb3
Source dataset
uspto-grants-2013_08
Patent number
US08513268B2

Reaction notes

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