p-Toluenesulfonic acid → Ethyl 3-amino-4-(trifluoromethyl)benzoate

HRID 1660177Notes

Reaction equation

HRID 1660177 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=C[CH:2]=1.[NH2:12][C:13]1[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][C:14]=1[C:22]([F:25])([F:24])[F:23].S([O-])([O-])(=O)=O.[Mg+2].[OH-].[Na+]>C1C=CC=CC=1.C(O)C>[CH2:1]([O:20][C:19]([C:17]1[CH:16]=[CH:15][C:14]([C:22]([F:23])([F:24])[F:25])=[C:13]([NH2:12])[CH:18]=1)=[O:21])[CH3:2]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 6426513-Amino-4-(trifluoromethyl)benzoic acid

Product 1

HCID 19783159Ethyl 3-amino-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

To a solution containing 5.62 g. of anhydrous p-toluenesulfonic acid pre-dissolved in 100 ml. of anhydrous ethanol and 500 ml. of benzene is added 6.1 g. of 2-amino-α,α,α-trifluoro-p-toluic acid. The solution is refluxed under an extractor containing a thimble of anhydrous magnesium sulfate for 11 days with periodic replacement of the drying agent. The resultant solution is then cooled, neutralized with 2 N sodium hydroxide and the organic layer is separated, washed with 2 N sodium hydroxide, and then with brine. After drying the organic solution over anhydrous magnesium sulfate, the solvents are removed on a rotary evaporator and the resulting crystals are dried to yield 2-amino-α,α,α-trifluoro-p-toluic acid ethyl ester (4-trifluoromethylanthranilic acid ethyl ester), m.p. 38°-39° C.

Workup

  1. additionTo a solution containing 5.62 g
  2. temperatureThe solution is refluxed under an extractor
  3. customthe organic layer is separated
  4. washwashed with 2 N sodium hydroxide
  5. dry with materialAfter drying the organic solution over anhydrous magnesium sulfate
  6. customthe solvents are removed on a rotary evaporator
  7. customthe resulting crystals are dried

Sources & evidence

ORD record
ord-1c9ad0bec0aa4d1598e5119a4d1d9d07
Source dataset
uspto-grants-1981_12
Patent number
US04307113

Reaction notes

Loading…