Water → N-(3-Chloro-4-cyano-2-methylphenyl)acetamide

HRID 2171591Notes

Reaction equation

HRID 2171591 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([CH3:12])[C:3]=1[Cl:13].[Cu](C#N)[C:15]#[N:16].O>CN(C=O)C>[Cl:13][C:3]1[C:4]([CH3:12])=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][C:2]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 962WaterHCID 86376N-(4-Bromo-3-chloro-2-methylphenyl)acetamideHCID 178418260HCID 178418260, compound

Product 1

HCID 58932655N-(3-Chloro-4-cyano-2-methylphenyl)acetamideYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of N-(4-bromo-3-chloro-2-methylphenyl)acetamide (45 g, 0.17 mol) and copper cyanide (34 g, 0.34 mol) in DMF (450 mL) was heated to 150° C. for 24 h. The suspension was cooled, poured into water with stirring. The solid was filtered and dried to give 25 g (70%) of the title compound which was used for the next step without further purification.

Workup

  1. temperatureThe suspension was cooled
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-6bcb8fbebd424b099bc6b67732f5cd89
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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