Methanol → Methyl 3-amino-4-(trifluoromethyl)benzoate

HRID 1475781Notes

Reaction equation

HRID 1475781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[CH2:15](OCC)C.CO.C[Si](C=[N+]=[N-])(C)C>CCCCCC>[CH3:15][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([C:11]([F:12])([F:13])[F:14])=[C:2]([NH2:1])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 167693Trimethylsilyldiazomethane2×HCID 6426513-Amino-4-(trifluoromethyl)benzoic acid

Product 1

HCID 15109485Methyl 3-amino-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

2.5 g of 3-Amino-4-trifluoromethyl-benzoic acid were dissolved using 50 ml of diethyl ether and 25 ml of methanol. Then, 6.1 ml of a 2M solution of trimethylsilyldiazomethane in hexane were added at 10-20° C. The reaction mixture was stirred at room temperature for 1 h. Then, 6.1 ml of a 2M solution of trimethylsilyldiazomethane in hexane were added at 10-20° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was then evaporated. Chromatography on silica gel using EA/HEP 1:2 yielded 2.3 g of the title compound, viscous oil.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 1 h
  2. customThe reaction mixture was then evaporated

Sources & evidence

ORD record
ord-c113f81035b145c9b50670a242e19b91
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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