Hydrochloric Acid → Methyl 2-Amino-4-(trifluoromethyl)benzoate

HRID 1672178Notes

Reaction equation

HRID 1672178 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].Cl.[CH3:16]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][CH3:16])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 678694-(Trifluoromethyl)anthranilic acid

Product 1

HCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoateYield 75%

Procedure

To a mixture of 2-amino-4-(trifluoromethyl)benzoic acid (150 g, 0.73 mol) in MeOH (2.5 L) was added conc. HCl (0.5 L, 16.5 mol). The reaction mixture was allowed to stir at reflux. After 3 h, an additional portion of HCl (0.5 L, 16.5 mol) was added and the reaction was allowed to continue to stir at 80° C. for 60 h. The reaction mixture was allowed to cool to rt and was concentrated. Water (0.5 L) was added to the residue, and the solution was basified with 10% aqueous NaOH solution. The resulting precipitate was filtered to give methyl 2-amino-4-(trifluoromethyl)benzoate (120 g, 75%) as a white solid.

Workup

  1. temperatureat reflux
  2. stirringto stir at 80° C. for 60 h
  3. concentrationwas concentrated
  4. additionWater (0.5 L) was added to the residue
  5. filtrationThe resulting precipitate was filtered

Sources & evidence

ORD record
ord-0a06169c883342688631d6997d8abcd8
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

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