Nitric Acid → N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

HRID 1761641Notes

Reaction equation

HRID 1761641 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[C:5]([N+:13]([O-:15])=[O:14])=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 589188N-(3-Chloro-4-fluorophenyl)acetamide

Product 1

HCID 2773811N-(5-chloro-4-fluoro-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of N-(3-chloro-4-fluorophenyl)acetamide (55 g) in concentrated sulfuric acid (165 ml) was added dropwise concentrated nitric acid (d 1.42, 154 ml) at 5°-10° C. during an hour with stirring in an ice-salt bath. After stirring for an hour at the same temperature, the reaction mixture was poured into ice water. The resulting precipitate was collected by filtration, sufficiently washed with water and recrystallized from acetonitrile to give the title compound (48.9 g) as yellow needles, mp 114°-115° C.

Workup

  1. stirringAfter stirring for an hour at the same temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washsufficiently washed with water
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-9e29a83732db4959a8020002b024b850
Source dataset
uspto-grants-1989_05
Patent number
US04826982

Reaction notes

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