HCID 68157911, compound → 1247120-24-6

HRID 243130Notes

Reaction equation

HRID 243130 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]=[CH:11][C:10]=2[F:15])[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]=[CH:11][C:10]=2[F:15])[C:5]([NH2:16])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157911HCID 68157911, compound

Product 1

HCID 623760701247120-24-6

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Fluoro-2-nitrophenyl)-(2-fluorophenyl)amine (3.04 g, 12.16 mmol) was dissolved in EtOAc (120 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 extra 2 h. The resultant mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound as a dark yellow oil, which solidified on standing (2.89 g, 95%). 1H NMR (CDCl3, 400 MHz): δ 7.05-6.87 (2H, m), 6.83-6.68 (3H, m), 6.68-6.59 (2H, m), 5.36 (1H, s), 3.49 (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 extra 2 h
  6. filtrationThe resultant mixture was filtered through Celite®
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-fd3cab791f594ed5adb0ecf400d19806
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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