Nitric Acid → N-(4-fluoro-2-methyl-6-nitrophenyl)acetamide

HRID 17547

Reaction equation

HRID 17547 reaction equation
[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:8]([CH3:16])[CH:7]=1>C(O)(=O)C>[F:5][C:6]1[CH:11]=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([NH:12][C:13](=[O:15])[CH3:14])=[C:8]([CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 2737623N-(4-Fluoro-2-methylphenyl)acetamide

Product 1

HCID 54330341N-(4-fluoro-2-methyl-6-nitrophenyl)acetamideYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

With cooling with ice, fuming nitric acid (25 ml) was dropwise added to an acetic acid (100 ml) solution of N-(4-fluoro-2-methylphenyl)acetamide (I-259) (10.0 g, 59.8 mmol), taking 50 minutes. After the addition, then restoration to room temperature and stirring for 23 hours, the reaction liquid was poured into ice. The precipitated solid was collected by filtration, washed with water, then dried to obtain the entitled compound (11.1 g, 87%) as a pale brown solid.

Workup

  1. additionAfter the addition
  2. customthe reaction liquid
  3. additionwas poured into ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-c0b4e5a56fc740aabdc16f007c2e158d
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Linked notes

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