Methanol → N-(3-Amino-4-chlorophenyl)acetamide

HRID 1870587Notes

Reaction equation

HRID 1870587 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[Na+].C([O-])(O)=O.[Na+].CO.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16](Cl)[C:15]=1[N+:24]([O-])=O>[Pt].O>[CH3:2][C:1]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[C:15]([NH2:24])[CH:16]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 3014625Benzene, 1,3-dichloro-2,4-dinitro-

Product 1

HCID 103996N-(3-Amino-4-chlorophenyl)acetamideYield 85%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

A hydrogenation reactor is charged with 15 parts of sodium acetate, 60 parts of NaHCO3, 1320 parts of MeOH and 1015 parts of 1-chloro-2,4-dinitrochlorobenzene under nitrogen at 50° C. and then 11 parts of 1% Pt/C, 0.15 parts of NH4VO3 and 66 parts of water are added.The hydrogenation is carried out at 60° C. and 18 bar. The product is isolated as 3-amino-4-chloroacetanilide (785 parts, 85% of theory).

Workup

  1. customis carried out at 60° C.

Sources & evidence

ORD record
ord-a6c2fb3fabda4893b012889bd6601f8d
Source dataset
uspto-grants-2000_08
Patent number
US06096924

Reaction notes

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