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

HRID 1479

Reaction equation

HRID 1479 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:5]([NH:6][C:7](=[O:9])[CH3:8])=[C:4]([F:15])[CH:3]=1.[H][H]>[Pt].C(O)C.O1CCCC1>[NH2:12][C:11]1[C:2]([Cl:1])=[CH:3][C:4]([F:15])=[C:5]([CH:10]=1)[NH:6][C:7](=[O:9])[CH3:8]

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)acetamide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A mixture of 4'-chloro-2'-fluoro-5'-nitroacetanilide (35.2 g, 151 mmol), and 5% platinum on carbon (7.0 g, 20 wt/wt %) in an ethanol/tetrahydrofuran (2:1) solution is hydrogenated until 28 psi of hydrogen is taken up. The reaction mixture is then filtered, and concentrated in vacuo to give the title product as a tan solid which is identified by 1H NMR spectral analysis.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdb5cf4636964e228521df4be25b6c2c
Source dataset
uspto-grants-1998_03
Patent number
US05726126

Linked notes

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