2-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid methyl ester → 3-Amino-2-cyclopropylamino-6-fluorobenzoic acid methyl ester

HRID 243109Notes

Reaction equation

HRID 243109 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([N+:11]([O-])=O)[C:5]=1[NH:14][CH:15]1[CH2:17][CH2:16]1>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=1[NH:14][CH:15]1[CH2:16][CH2:17]1

Participants

3

Reactant 1

HCID 681576262-Cyclopropylamino-6-fluoro-3-nitrobenzoic acid methyl ester

Product 1

HCID 681570823-Amino-2-cyclopropylamino-6-fluorobenzoic acid methyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-cyclopropylamino-6-fluoro-3-nitrobenzoic acid methyl ester (865 mg, 3.40 mmol) in EtOAc (25 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (116 mg) and was stirred at RT under a hydrogen atmosphere for 20 h. The suspension was filtered and the filtrate was concentrated in vacuo to afford the title compound as a dark yellow oil (756 mg, 99%). LCMS (Method C): RT 2.29 min [M+H]+ 225.18.

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (116 mg)
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1d8bc6e1936f420d9550ea526289b3d1
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…