HCID 55067914, compound → HCID 62375897, compound

HRID 243136Notes

Reaction equation

HRID 243136 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=2[N+:15]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O>[CH:1]1([NH:7][C:8]2[C:9]([NH2:15])=[CH:10][CH:11]=[C:12]([F:14])[CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 55067914HCID 55067914, compound

Product 1

HCID 62375897HCID 62375897, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(Cyclohexyl-(5-fluoro-2-nitrophenyl)amine (2.4 g, 10.0 mmol) was dissolved in EtOAc (40 mL) and the flask evacuated and flushed with nitrogen gas. 10% Pd/C (0.24 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas, at RT overnight. The resultant mixture was filtered through Celite® and the filtrate was concentrated in vacuo to afford the title compound as a dark red oil (1.9 g, 92%). 1H NMR (CDCl3, 400 MHz): δ 6.61 (1H, dd, J=8.35, 5.74 Hz), 6.35 (1H, dd, J=11.23, 2.77 Hz), 6.27 (1H, td, J=8.43, 2.76 Hz), 3.23-3.11 (1H, m), 2.11-2.00 (2H, m), 1.83-1.72 (2H, m), 1.70-1.60 (1H, m), 1.47-1.12 (5H, m)

Workup

  1. customthe flask evacuated
  2. customflushed with nitrogen gas
  3. addition10% Pd/C (0.24 g) was added
  4. filtrationThe resultant mixture was filtered through Celite®
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ceeb5715e5eb41389497b3a22c722ad3
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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