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

HRID 328287Notes

Reaction equation

HRID 328287 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO.B(F)(F)F.[CH3:21]COCC.C(=O)([O-])[O-].[Na+].[Na+]>O>[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:21])=[O:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 10340Sodium CarbonateHCID 678694-(Trifluoromethyl)anthranilic acid

Product 1

HCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-trifluoromethyl-benzoic acid (141.2 g.), methanol (1.51 liters) and boron trifluoride etherate (506 cc.) are heated to the reflux temperature for 99 hours. The solution obtained is added to sodium carbonate (350 g.) in iced water (2.8 kg.). The mixture is stirred for 15 minutes and is then extracted with ethyl ether (3 liters). The ether layer is washed with water (250 cc.) and then dried over anhydrous magnesium sulphate (30 g.). After filtration and concentration, methyl 2-amino-4-trifluoromethyl-benzoate (137 g.) melting at 64° C is obtained.

Workup

  1. customThe solution obtained
  2. extractionis then extracted with ethyl ether (3 liters)
  3. washThe ether layer is washed with water (250 cc.)
  4. dry with materialdried over anhydrous magnesium sulphate (30 g.)
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-ec858cfbc4d14285bf17f52aee9e27be
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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