5-fluoro-N-(3-fluorophenyl)-2-nitroaniline → 4-Fluoro-N2-(3-fluorophenyl)benzene-1,2-diamine

HRID 243128Notes

Reaction equation

HRID 243128 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:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[CH:7]=1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 584593185-fluoro-N-(3-fluorophenyl)-2-nitroaniline

Product 1

HCID 584592724-Fluoro-N2-(3-fluorophenyl)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Fluoro-2-nitrophenyl)-(3-fluorophenyl)amine (2.79 g, 11.16 mmol) was dissolved in EtOAc (110 mL) and the flask evacuated and flushed with nitrogen gas. 10% Pd/C (0.3 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas, at RT overnight. A further amount of 10% Pd/C (0.3 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas for an further 2 h. The resultant mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound as a brown oil, which solidified on standing (2.57 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.17 (1H, td, J=8.16, 6.58 Hz), 6.94-6.87 (1H, m), 6.76-6.70 (2H, m), 6.62-6.47 (3H, m), 5.35 (1H, s), 3.54 (2H, s)

Workup

  1. customthe flask evacuated
  2. customflushed with nitrogen gas
  3. addition10% Pd/C (0.3 g) was added
  4. additionA further amount of 10% Pd/C (0.3 g) was added
  5. stirringthe reaction mixture stirred under an atmosphere of hydrogen gas for an further 2 h
  6. filtrationThe resultant mixture was filtered through Celite®
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-7368495834d34b09907b83ed1d1c2836
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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