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

HRID 432948Notes

Reaction equation

HRID 432948 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>C(OCC)(=O)C.[Ni]>[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

4

Reactant 1

HCID 13563753N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide

Product 1

HCID 11769584N-(5-amino-4-chloro-2-fluorophenyl)acetamideYield 93.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
77.5 °C

Procedure

In a 1 L autoclave, 23.25 g (0.1 mole) of N-(4-chloro-2-fluoro-5-nitrophenyl)acetamide and 1.2 g of Ni-catalyst were suspended under nitrogen in 500 mL of ethyl acetate. The autoclave was purged two times with nitrogen at 500 kPa (5 atmospheres) and once with hydrogen at 500 kPa (5 atmospheres). 500 kPa (5 atmospheres) of hydrogen was then applied and the reactor heated to 75-80° C. After 6 hours the autoclave was cooled to room temperature. The catalyst was filtered off and the solvent removed under reduced pressure. The solid was triturated with petroleum ether and filtered to give 18.9 g of the title compound as a crystalline solid melting at 142-143° C. (purity: 99.4% by HPLC).

Workup

  1. customThe autoclave was purged two times with nitrogen at 500 kPa (5 atmospheres)
  2. temperatureAfter 6 hours the autoclave was cooled to room temperature
  3. filtrationThe catalyst was filtered off
  4. customthe solvent removed under reduced pressure
  5. customThe solid was triturated with petroleum ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cbcc0c20906e4f26a3fa5cefcf40c56d
Source dataset
uspto-grants-2003_12
Patent number
US06664400B2

Reaction notes

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