2'-Chloro-4'-fluoro-5'-nitroacetanilide → 5'-Amino-2'-chloro-4'-fluoroacetanilide

HRID 380797Notes

Reaction equation

HRID 380797 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([N+:13]([O-])=O)=[CH:8][C:3]=1[NH:4][C:5](=[O:7])[CH3:6]>[Pt].O1CCCC1.C(OCC)(=O)C.C(O)C>[NH2:13][C:9]1[C:10]([F:12])=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[NH:4][C:5](=[O:7])[CH3:6]

Participants

4

Reactant 1

HCID 183659292'-Chloro-4'-fluoro-5'-nitroacetanilide

Product 1

HCID 183659355'-Amino-2'-chloro-4'-fluoroacetanilide

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 18365940Tetrahydrofuran ethyl acetate ethanolSolvent

Procedure

A mixture of 2′-chloro-4′-fluoro-5′-nitroacetanilide (26.1 g, 112 mmol) and 5% platinum on carbon (7.8 g, 30 wt %) in a tetrahydrofuran/ethyl acetate/ethanol solution (1:1:1) is hydrogenated at 50 psi for 22 hours and filtered. The resultant filtrate is concentrated in vacuo to obtain a solid which is recrystallized from an ethanol/water solution to give the title product as off-white plates (14.5 g, mp 176-178° C.).

Workup

  1. filtrationfiltered
  2. concentrationThe resultant filtrate is concentrated in vacuo
  3. customto obtain a solid which
  4. customis recrystallized from an ethanol/water solution

Sources & evidence

ORD record
ord-b903eb748ad94809a5f45a9ac72ee422
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

Loading…