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

HRID 243104

Reaction equation

HRID 243104 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=2)[CH:7]=1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([F:15])[CH:14]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157752(5-Fluoro-2-nitrophenyl)-(5-fluoropyridin-3-yl)amine

Product 1

HCID 681580564-Fluoro-N2-(5-fluoropyridin-3-yl)benzene-1,2-diamineYield 105.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (5-fluoro-2-nitro-phenyl)-(5-fluoropyridin-3-yl)amine (425 mg, 1.69 mmol) in EtOAc (30 mL) was degassed with a stream of nitrogen prior to addition of 10% Pd/C (50 mg) and was stirred at RT under a hydrogen atmosphere for 19 h. The mixture was filtered and the filtrate concentrated in vacuo to afford the title compound as a brown solid (395 mg, quantitative). LCMS (Method C): RT 2.24 min [M+H]+ 222.07

Workup

  1. customwas degassed with a stream of nitrogen
  2. additionto addition of 10% Pd/C (50 mg)
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-1fd6f62bcd984096920bd4bbb395f7c8
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Linked notes

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