(5-Fluoro-2-nitrophenyl)-(3-fluoropyridin-2-yl)amine → 4-Fluoro-N2-(3-fluoropyridin-2-yl)benzene-1,2-diamine

HRID 243114Notes

Reaction equation

HRID 243114 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([NH:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:7]=1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][N:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68158108(5-Fluoro-2-nitrophenyl)-(3-fluoropyridin-2-yl)amine

Product 1

HCID 681569974-Fluoro-N2-(3-fluoropyridin-2-yl)benzene-1,2-diamineYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-fluoro-2-nitro-phenyl)-(3-fluoropyridin-2-yl)amine (93 mg, 0.370 mmol) in EtOAc (10 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (10 mg) and was stirred at RT under a hydrogen atmosphere for 3 h. The mixture was then filtered through a phase separator and the filtrate was concentrated in vacuo to afford the title compound as a brown solid (81 mg, 99%). LCMS (Method C): RT 1.70 min [M+H]+ 222.18.

Workup

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

Sources & evidence

ORD record
ord-cae598f10d5840f49f254449b561ac02
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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