Acetic Anhydride → 2-Acetamido-alpha,alpha,alpha-trifluoro-p-toluic acid

HRID 1660178Notes

Reaction equation

HRID 1660178 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[C:15]([NH:1][C:2]1[CH:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14])(=[O:17])[CH3:16]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 6426513-Amino-4-(trifluoromethyl)benzoic acid

Product 1

HCID 151094842-Acetamido-alpha,alpha,alpha-trifluoro-p-toluic acid

Procedure

3 g. of 2-amino-α,α,α-trifluoro-p-toluic acid is dissolved in 20 ml. of acetic anhydride and the resultant solution is heated to 80° C. After 30 minutes at a temperature of 80° C., the excess acetic anhydride is removed from the reaction mixture on a rotary evaporator and water is added to the residue. The resultant precipitate is filtered, washed with water and dried to yield 2-acetamido-α,α,α-trifluoro-p-toluic acid (N-acetyl-4-trifluoromethylanthranilic acid), m.p. 195°-197° C.

Workup

  1. customthe excess acetic anhydride is removed from the reaction mixture on a rotary evaporator and water
  2. additionis added to the residue
  3. filtrationThe resultant precipitate is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b48138085a8042e79467c08d614181f7
Source dataset
uspto-grants-1981_12
Patent number
US04307113

Reaction notes

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