Nitric Acid → n-(3-chloro-4-nitrophenyl)acetamide

HRID 1773581Notes

Reaction equation

HRID 1773581 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][CH:7]=1.[N+:12]([O-])([OH:14])=[O:13]>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 114933-Chloroacetanilide

Product 1

HCID 236820n-(3-chloro-4-nitrophenyl)acetamide

Conditions

Temperature
-20 °C

Procedure

Fuming nitric acid (150 mL) was slowly added, at −50° C., over a period of 50 minutes to N-(3-chloro-phenyl)-acetamide (45 g). The reaction mixture was allowed to warm up to −20° C. and then was poured into ice-water. The solid formed was collected by filtration, washed with water, and dried under reduced pressure. The residue was washed with dichloromethane and dried under reduced pressure to afford 14 g of N-(3-chloro-4-nitro-phenyl)-acetamide as a light pink solid.

Workup

  1. customThe solid formed
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried under reduced pressure
  5. washThe residue was washed with dichloromethane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a8b2617b58784ac5a8356462ff14b90e
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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