N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide → N-(5-amino-4-chloro-2-fluorophenyl)acetamide

HRID 1107248Notes

Reaction equation

HRID 1107248 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([F:15])[CH:3]=1.[H][H]>C(OCC)(=O)C.[Ir]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([F:15])=[C:5]([NH:11][C:12](=[O:14])[CH3:13])[CH:6]=1

Participants

5

Reactant 2

HCID 13563753N-(4-chloro-2-fluoro-5-nitrophenyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamideYield 98.1%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a supension of the title compound of Step A (116 g, 500 mmol) in 500 mL of ethyl acetate was added 3.63 g of iridium (5%) on charcoal. The hydrogenation was performed at 4 bar of hydrogen pressure in an autoclave for 4.5 h at 60° C. The reaction was then filtered and the solvent removed under reduced pressure. Drying of the crystalline product yielded the title compound of Step B (99.4 g, 98%) melting at 142-143° C. 1H NMR (CDCl3) δ 7.9 (d, 1H), 7.3-7.2 (br s, 1H), 7.1-7.0 (s, 2H), 2.2-2.1 (s, 3H).

Workup

  1. filtrationThe reaction was then filtered
  2. customthe solvent removed under reduced pressure
  3. customDrying of the crystalline product

Sources & evidence

ORD record
ord-1239f49ee7aa4bcca3cc66bf58b950c2
Source dataset
uspto-grants-2000_05
Patent number
US06060432

Reaction notes

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