Potassium Nitrate → 4-Amino-3-nitrobenzonitrile

HRID 373073Notes

Reaction equation

HRID 373073 reaction equation
C([NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)(=O)C.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[NH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][C:6]=1[N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 37256N-(4-cyanophenyl)acetamide

Product 1

HCID 5959014-Amino-3-nitrobenzonitrile

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-acetamidobenzonitrile (9.40 g) in concentrated sulfuric acid (80 ml) was added potassium nitrate in small portions at a temperature not exceeding 10° C. The reaction mixture was stirred at 5°-10° C. for 2 hours and poured into ice-water and the separated crystals were collected by suction. To the crystals was added 4N hydrochloric acid (100 ml) and the mixture was refluxed for 2 hours. After cooling to room temperature, the crystals were recovered by filtration, washed with water and dried under reduced pressure to give 7.22 g of 4-amino-3-nitrobenzonitrile.

Workup

  1. customexceeding 10° C
  2. customthe separated crystals were collected by suction
  3. additionTo the crystals was added 4N hydrochloric acid (100 ml)
  4. temperaturethe mixture was refluxed for 2 hours
  5. filtrationthe crystals were recovered by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3d5360a9ffbd4cfb90f9ebf441966788
Source dataset
uspto-grants-1992_11
Patent number
US05162318

Reaction notes

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