Acetaldehyde → 2-Ethylamino-alpha,alpha,alpha-trifluoro-p-toluic acid ethyl ester

HRID 1660179Notes

Reaction equation

HRID 1660179 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[C:8]([NH2:16])[CH:7]=1)=[O:5])[CH3:2].[CH:17](=O)[CH3:18]>[Pd].C(O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:13])([F:15])[F:14])=[C:8]([NH:16][CH2:17][CH3:18])[CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 177AcetaldehydeHCID 19783159Ethyl 3-amino-4-(trifluoromethyl)benzoate

Product 1

HCID 867381682-Ethylamino-alpha,alpha,alpha-trifluoro-p-toluic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 0.466 g. of 2-amino-α,α,α-trifluoro-p-toluic acid ethyl ester (prepared according to the procedure described in Example 2) predissolved in 20 ml. of anhydrous ethanol is added 5 ml. of 31% aqueous acetaldehyde and 46 mg. of 10% palladium on carbon. The resultant mixture is then hydrogenated at 60° for 18 hours. The reaction mixture is then cooled, filtered, the solvent removed, and the resultant oil is chromatographed on preparative thin layer plates to yield 2-ethylamino-α,α,α-trifluoro-p-toluic acid ethyl ester (N-ethyl-4-trifluoromethylanthranilic acid ethyl ester).

Workup

  1. temperatureThe reaction mixture is then cooled
  2. filtrationfiltered
  3. customthe solvent removed
  4. customthe resultant oil is chromatographed on preparative thin layer plates

Sources & evidence

ORD record
ord-f1c6d62d0be04db888565729185a2a7f
Source dataset
uspto-grants-1981_12
Patent number
US04307113

Reaction notes

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