Diazomethane → Methyl 2-Amino-4-(trifluoromethyl)benzoate

HRID 522375Notes

Reaction equation

HRID 522375 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].[N+](=[CH2:17])=[N-]>C1COCC1.CCOCC>[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][CH3:17])=[O:5]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 678694-(Trifluoromethyl)anthranilic acid

Product 1

HCID 12601886Methyl 2-Amino-4-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-(trifluoromethyl)benzoic acid (5 g) in THF (85 ml) was added diazomethane (48.7 ml) in ether until completion of the reaction. Nitrogen was bubbled into the reaction mixture for 15 minutes to remove the excess of diazomethane and the solvent was removed under reduced pressure to provide a light brown solid (5.34 g). The compound was used in the next without purification. LRMS (ES+) m/z 220.1 (M+H)+.

Workup

  1. customuntil completion of the reaction
  2. customNitrogen was bubbled into the reaction mixture for 15 minutes
  3. customto remove the excess of diazomethane
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-49cd6410aa0c4f8f86c07993bafe75b7
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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