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

HRID 1087127Notes

Reaction equation

HRID 1087127 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)(=[O:7])[CH3:6]>O>[C:5]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:1]([O-:4])=[O:2])=[C:11]([Cl:15])[CH:10]=1)(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 114933-Chloroacetanilide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To fuming nitric acid (120 mL) at -50° C. was added N-acetyl-3-chloroaniline (30 g) over a period of 45 minutes. The reaction was kept between -50° C. and -30° C. using a dry ice/acetone bath. The reaction mixture was stirred for an additional hour and then poured into 1500 mL of crushed ice and water. The precipitate was filtered and slurried with 1 liter of slightly alkaline water (ammonium hydroxide) twice. The precipitate was then dried and recrystallized from toluene to yield (3.6 g) of N-acetyl-3-chloro-4-nitroaniline; m.p. 134°-136° C.

Workup

  1. customwas kept between -50° C. and -30° C.
  2. filtrationThe precipitate was filtered
  3. customThe precipitate was then dried
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-78a991295e1e4baf93b5315f3fafa37a
Source dataset
uspto-grants-1991_07
Patent number
US05034410

Reaction notes

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