Sodium Cyanide → Methyl 1-cyanoindan-4-carboxylate

HRID 1606723Notes

Reaction equation

HRID 1606723 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. The, 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-bdc401635d634dbeafdde66aa9afa802
Source dataset
uspto-grants-1976_04
Patent number
US03953500

Reaction notes

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