HCID 68157885, compound → HCID 62377108, compound

HRID 243133Notes

Reaction equation

HRID 243133 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[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]([O:15][CH3:16])[CH:10]=2)[C:5]([NH2:17])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157885HCID 68157885, compound

Product 1

HCID 62377108HCID 62377108, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(5-Fluoro-2-nitrophenyl)-(3-methoxyphenyl)amine (3.35 g, 12.7 mmol) was dissolved in EtOAc (50 mL) and the flask evacuated and flushed with nitrogen gas. 10% Pd/C (0.35 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas, at RT overnight. A further amount of 10% Pd/C (0.35 g) was added and the reaction mixture stirred under an atmosphere of hydrogen gas for a further 1 h. The resultant mixture was filtered through Celite® and the filtrate concentrated in vacuo to afford the title compound as a red gum (2.97 g, 100%). 1H NMR (CDCl3, 400 MHz): δ 7.15 (1H, t, J=8.08 Hz), 6.91 (1H, dd, J=9.89, 2.72 Hz), 6.76-6.62 (2H, m), 6.49-6.37 (3H, m), 5.29 (1H, s), 3.77 (3H, s), 3.52 (2H, s)

Workup

  1. customthe flask evacuated
  2. customflushed with nitrogen gas
  3. addition10% Pd/C (0.35 g) was added
  4. additionA further amount of 10% Pd/C (0.35 g) was added
  5. stirringthe reaction mixture stirred under an atmosphere of hydrogen gas for a further 1 h
  6. filtrationThe resultant mixture was filtered through Celite®
  7. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-12b557acd3994a028babc632900508dc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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