Sodium Cyanide → (2-Methyl-3-nitrophenyl)acetonitrile

HRID 1436855Notes

Reaction equation

HRID 1436855 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:8]=1[CH3:16])(=O)=O.[C-:17]#[N:18].[Na+]>C(#N)C.O>[CH3:16][C:8]1[C:9]([N+:13]([O-:15])=[O:14])=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:17]#[N:18]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 193697582-Methyl-3-nitrobenzyl methanesulfonate

Product 1

HCID 13530896(2-Methyl-3-nitrophenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
87.5 °C

Procedure

2-Methyl-3-nitrobenzyl methanesulfonate (207 g ) dissolved in Acetonitrile (625 ml). A solution of (41.5 g) sodium cyanide in 200 ml pure water was added to the above solution and refluxed at 80-95° C. until the completion of reaction. Acetonitrile was distilled out and 1000 ml water was added to the residue followed by addition of 1000 ml dichloromethane. The mixture was stirred for 15 minutes followed by extraction. Dichloromethane is distilled out from organic layer and Cyclohexane is to the residue and stirred for 30 minutes to get 2-Methyl-3-nitro-phenylacetonitrile. It is filtered and dried to give 2-Methyl-3-nitro phenylacetonitrile (150-160 g) as brown solid.

Workup

  1. distillationAcetonitrile was distilled out
  2. addition1000 ml water was added to the residue
  3. additionfollowed by addition of 1000 ml dichloromethane
  4. extractionfollowed by extraction
  5. distillationDichloromethane is distilled out from organic layer and Cyclohexane
  6. stirringstirred for 30 minutes

Sources & evidence

ORD record
ord-cc4947a612594768aa6e0e47d7fb87c3
Source dataset
uspto-grants-2009_11
Patent number
US07619095B2

Reaction notes

Loading…