Nitric Acid → N-(5-Fluoro-2-nitrophenyl)acetamide

HRID 463601Notes

Reaction equation

HRID 463601 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)=[O:3].[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[CH3:1][C:2]([NH:4][C:5]1[CH:6]=[C:7]([F:11])[CH:8]=[CH:9][C:10]=1[N+:12]([O-:14])=[O:13])=[O:3]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 9594N-(3-Fluorophenyl)acetamide

Product 1

HCID 16641156N-(5-Fluoro-2-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

N-methylcarbonyl 3-fluoroaniline (5 g, 32.0 mmol) is dissolved in 25 ml of conc. sulfuric acid and is cooled to 0°. A mixture of 90% nitric acid (2.5 ml) in conc. sulfuric acid (25 ml) is added dropwise over a period of about 1 hour, with the temperature maintained at 0°. The reaction is allowed to warm to RT and is stirred at RT for 3 hours. The reaction is then carefully poured into ice. The resulting solid is washed several times with 10% ethyl acetate/hexane, and the combined organic extracts are stripped to give N-methylcarbonyl 2-nitro-5-fluoroaniline.

Workup

  1. temperatureis cooled to 0°
  2. additionis added dropwise over a period of about 1 hour, with the temperature
  3. temperaturemaintained at 0°
  4. additionThe reaction is then carefully poured into ice
  5. washThe resulting solid is washed several times with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c2ff3960e1874e1cafdbf86cdc9c48f4
Source dataset
uspto-grants-1985_10
Patent number
US04544400

Reaction notes

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