Nitric Acid → N-(4,5-Difluoro-2-nitrophenyl)acetamide

HRID 414371Notes

Reaction equation

HRID 414371 reaction equation
[F: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>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[C:5]([N+:13]([O-:15])=[O:14])[CH:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 223109N-(3,4-Difluorophenyl)acetamide

Product 1

HCID 540127N-(4,5-Difluoro-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of N-(3,4-difluorophenyl)acetamide (48 g) in concentrated sulfuric acid (140 ml) was added dropwise concentrated nitric acid (d 1.42, 56 ml) at -1° to 3° C. during 50 minutes with stirring in an ice-salt bath. After stirring for 1.5 hours at 3° to 16° C., the reaction mixture was poured into ice water (560 ml). The resulting precipitate was collected by filtration, washed with chilled water sufficiently to give N-(4,5-difluoro-2-nitrophenyl)acetamide (55.3 g).

Workup

  1. stirringAfter stirring for 1.5 hours at 3° to 16° C.
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with chilled water sufficiently

Sources & evidence

ORD record
ord-b01e7ee16e934511a93edd53e198398c
Source dataset
uspto-grants-1988_12
Patent number
US04791225

Reaction notes

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