Sodium Cyanide → Methyl 1-cyanoindan-4-carboxylate

HRID 436159Notes

Reaction equation

HRID 436159 reaction equation
Cl[CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1.[C-:15]#[N:16].[Na+]>CS(C)=O>[C:15]([CH:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=2[CH2:4][CH2:3]1)#[N:16]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 20310089Methyl 1-chloroindan-4-carboxylate

Product 1

HCID 12422074Methyl 1-cyanoindan-4-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In 80 ml. of dimethylsulfoxide is dissolved 15 g. of methyl 1-chloroindan-4-carboxylate and the solution is stirred. Then, 5.3 g. of sodium cyanide is added, followed by stirring for 8 hours. Following the addition of 750 ml. of water, the reaction mixture is extracted with ether. The extract is washed with a saturated aqueous solution of sodium chloride and, then, dried. The solvent is distilled off under reduced pressure and the residue is purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform). The described procedure gives methyl 1-cyanoindan-4-carboxylate as crystals melting at 76.5°-77.5° C.

Workup

  1. additionthe addition of 750 ml
  2. extractionof water, the reaction mixture is extracted with ether
  3. washThe extract is washed with a saturated aqueous solution of sodium chloride
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is purified by column chromatography on silica gel (500 g. silica gel; eluant: chloroform)

Sources & evidence

ORD record
ord-758b2b7dada54a2f8cd553bbb15c3100
Source dataset
uspto-grants-1977_02
Patent number
US04007225

Reaction notes

Loading…