Chloroacetic Acid → 2-chloro-N-(2-nitrophenyl)acetamide

HRID 1381186Notes

Reaction equation

HRID 1381186 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Cl:11][CH2:12][C:13](O)=[O:14]>O>[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:13](=[O:14])[CH2:12][Cl:11])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 69462-Nitroaniline

Product 1

HCID 2224432-chloro-N-(2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30 Grams of o-nitroaniline and 55.7 g of anhydrous chloroacetic acid were mixed together and the mixture was heated at 70° to 80° C. for 30 minutes with stirring, then water was added to the reaction mixture, the crystals thus formed were collected by filtration and recrystallized from isopropyl ether to obtain 49.42 g of o-nitro-α-chloroacetanilide in the form of light yellow flake-like crystals. Melting point: 85.5°-87.0° C.

Workup

  1. temperaturethe mixture was heated at 70° to 80° C. for 30 minutes
  2. customthe crystals thus formed
  3. filtrationwere collected by filtration
  4. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-8b4416f0bfe9482ab4b78d7bc4fc0c7c
Source dataset
uspto-grants-1986_04
Patent number
US04585774

Reaction notes

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