Methanol → Methyl 4-amino-2-(trifluoromethyl)benzoate

HRID 906192Notes

Reaction equation

HRID 906192 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.CO.[CH3:17][Si](C=[N+]=[N-])(C)C>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 38363254-amino-2-(trifluoromethyl)benzoic Acid

Product 1

HCID 46311081Methyl 4-amino-2-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Amino-2-(trifluoromethyl)benzoic acid (10 g, 48.8 mmol) was suspended in THF (100 mL) and methanol (30 mL) and was cooled in an ice bath. (Trimethylsilyl)diazomethane (2 M solution in hexanes; 32 mL) was added drop-wise. The mixture was stirred for 5 minutes and then concentrated to afford methyl 4-amino-2-(trifluoromethyl)benzoate (quantitative yield) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 7.78 (d, 1H), 6.99 (d, 1H), 6.77 (d, 1H), 4.18 (br s, 2H), 3.88 (s, 3H); GCMS for C9H8F3NO2: 219 (M+).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-fac36f1afa3a44eeb81552411bca27bf
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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