Sodium Cyanide → HCID 13501071, compound

HRID 330261Notes

Reaction equation

HRID 330261 reaction equation
Br[CH2:2][C:3]1[C:12]([CH3:13])=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.[C-:14]#[N:15].[Na+]>O>[CH3:13][C:12]1[C:3]([CH2:2][C:14]#[N:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 27530932-Bromomethyl-3-methylnaphthalene

Product 1

HCID 13501071HCID 13501071, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2-bromomethyl3-methylnaphthalene (2.87 g, 12.2 mmol) and NaCN (652 mg, 13.3 mmol) in CH3CH/H2O (9:1, 125 mL) was heated to reflux for 1 hour. Upon warming, the suspension became homogeneous. After cooling to room temperature, the volatiles were removed from the reaction mixture in vacuo and the residue was partitioned between 2O (150 mL) and CH2Cl2 (150 mL). The aqueous phase was extracted with CH2Cl2 (1×150 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (2.18 g, 99%). This material was of sufficient purity to be used as such in the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperatureUpon warming
  4. customthe volatiles were removed from the reaction mixture in vacuo
  5. customthe residue was partitioned between 2O (150 mL) and CH2Cl2 (150 mL)
  6. extractionThe aqueous phase was extracted with CH2Cl2 (1×150 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a41d8d0dfd640d6b7d006b46d689e4b
Source dataset
uspto-grants-1990_01
Patent number
US04895861

Reaction notes

Loading…