HCID 54527561, compound → HCID 13530360, compound

HRID 243126Notes

Reaction equation

HRID 243126 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][C:12]([F:15])=[CH:11][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][C:12]([F:15])=[CH:11][CH:10]=2)[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54527561HCID 54527561, compound

Product 1

HCID 13530360HCID 13530360, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Fluoro-2-nitrophenyl)-(4-fluorophenyl)amine (2.94 g, 11.76 mmol) was dissolved in EtOAc (120 mL) and the flask evacuated and flushed with nitrogen gas. 10% Pd/C (0.29 g) was added and the reaction mixture stirred at RT, under an atmosphere of hydrogen overnight. The resultant mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound as an orange oil (2.67 g, 91%). 1H NMR (CDCl3, 400 MHz): δ 7.01-6.92 (2H, m), 6.87-6.68 (4H, m), 6.61 (1H, td, J=8.35, 2.79 Hz), 5.24 (1H, s), 3.46 (2H, s)

Workup

  1. customthe flask evacuated
  2. customflushed with nitrogen gas
  3. addition10% Pd/C (0.29 g) was added
  4. filtrationThe resultant mixture was filtered through Celite®
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-6ed619b8c2b6485c83b92972ed50ca7f
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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