Potassium Cyanide → HCID 21865581, compound

HRID 896656Notes

Reaction equation

HRID 896656 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([Br:13])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[C-:14]#[N:15].[K+]>O>[Br:13][C:11]1[CH:12]=[C:3]([CH2:2][C:14]#[N:15])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 155413198-Bromo-6-(bromomethyl)quinoline

Product 1

HCID 21865581HCID 21865581, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

DMP (10 mL) and H2O (5 mL) were added to 6-bromomethyl-8-bromoquinoline (3 g) (described in International Patent Publication WO 94/22852) and potassium cyanide (1.6 g). After heating at 100° C. for 1 hour, the resulting mixture was quenched with H2O (100 mL) and extracted with EtOAc. The combined organic extracts were washed with water (3×), brine, dried over MgSO4, filtered and concentrated. Flash chromatography (hexane:EtOAc, 3:1) yielded the (8-Bromo-quinolin-6-yl)-acetonitrile compound as a white solid.

Workup

  1. customthe resulting mixture was quenched with H2O (100 mL)
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water (3×), brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cfa8ce18334349a3a6be74dc56166673
Source dataset
uspto-grants-2005_07
Patent number
US06919353B2

Reaction notes

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