Sodium Cyanide → HCID 13393251, compound

HRID 2309234Notes

Reaction equation

HRID 2309234 reaction equation
[CH:1]([CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5]1=[O:14])=[O:2].S(=O)(O)[O-].[Na+].[C-:20]#[N:21].[Na+]>O.CCOCC>[C:20]([CH:1]([OH:2])[CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:13])[C:5]1=[O:14])#[N:21]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 20186084HCID 20186084, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13393251HCID 13393251, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

89 Grams of 3-formylmethyl-1-methyloxindole and 54 g of sodium bisulfite was dissolved in a mixed solvent of 75 ml of water with 150 ml of ether, then to the resultant mixture was added dropwise a solution of 28 g of sodium cyanide with 60 ml of water, under stirring at a room temperature. The reaction mixture was stirred for 1 hour, then water was added to the reaction mixture until the crystals formed were dissolved, the whole reaction mixture was further stirred for 1 hour. The crystals formed were collected by filtration, washed with water, dried and recrystallized from benzene to obtain 30 g of 3-(2-cyano2-hydroxyethyl)-1-methyloxindole in the form of white powdery substance. Melting point: 136°-138°C.)

Workup

  1. stirringThe reaction mixture was stirred for 1 hour
  2. customformed
  3. dissolutionwere dissolved
  4. customthe whole reaction mixture
  5. stirringwas further stirred for 1 hour
  6. customThe crystals formed
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customdried
  10. customrecrystallized from benzene

Sources & evidence

ORD record
ord-515d5f0f405147dc87733f205c0d9fc1
Source dataset
uspto-grants-1987_09
Patent number
US04694017

Reaction notes

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