Potassium Nitrate → 4-Chloro-2-methyl-5-nitrobenzonitrile

HRID 724165Notes

Reaction equation

HRID 724165 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[N+:11]([O-])([O-:13])=[O:12].[K+]>OS(O)(=O)=O>[Cl:1][C:2]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 1427424-Chloro-2-methylbenzonitrile

Product 1

HCID 106555244-Chloro-2-methyl-5-nitrobenzonitrileYield 42.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 4-chloro-2-methylbenzonitrile (10 g, 66 mmol) in conc. H2SO4 was added KNO3 (7.0 g, 69.3 mmol) at 0° C. in small portions, and then the reaction mixture was stirred overnight at ambient temperature. It was then poured into ice and extracted with AcOEt. The combined extracts were washed by sat. NaHCO3 aq., dried over MgSO4 and concentrated. The resulting precipitates were collected by filtration, washed with ether, and dried under reduced pressure to give 5.5 g (42%) of the title compound.

Workup

  1. additionIt was then poured into ice
  2. extractionextracted with AcOEt
  3. washThe combined extracts were washed by sat. NaHCO3 aq.
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration
  8. washwashed with ether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-a37792f823df420b80b50ba76a7eced0
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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