3-Fluoro-2-nitro-N-phenylaniline → HCID 44254861, compound

HRID 242816Notes

Reaction equation

HRID 242816 reaction equation
[F:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]=1[NH2:15]

Participants

4

Reactant 1

HCID 442552223-Fluoro-2-nitro-N-phenylaniline

Product 1

HCID 44254861HCID 44254861, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (3-fluoro-2-nitrophenyl)phenylamine (1.06 g, 4.56 mmol) and 10% Pd/C (100 mg) in EtOAc (20 mL) was degassed with a stream of nitrogen and stirred at RT under a hydrogen atmosphere for 7 h. The suspension was then filtered through a PTFE frit and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% EtOAc in cyclohexane) affording 3-Fluoro-N1-phenylbenzene-1,2-diamine (440 mg, 48%). LCMS: RT 3.46 min [M+H]+ 203.1.

Workup

  1. customwas degassed with a stream of nitrogen
  2. filtrationThe suspension was then filtered through a PTFE frit
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-20% EtOAc in cyclohexane)

Sources & evidence

ORD record
ord-7a3764df5e804b42a16b1c4e575ab2b6
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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