Potassium Cyanide → HCID 21865581, compound

HRID 857277Notes

Reaction equation

HRID 857277 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+]>CN(C=O)C.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 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution 6-bromomethyl-8-bromoquinoline (described in International Patent Publication WO 94/22852) (1.0 eq) in DMF:H2O (2:1, 0.66M) was added potassium cyanide (2.5 eq). After heating at 100° C. for 1 h, the resulting mixture was quenched with H2O and extracted with EtOAc (2 x). The combined organic extracts were washed with water (3×), brine, dried over MgSO4, filtered and concentrated. Flash chromatography (Hex:EtOAc, 3:1) yielded the desired compound as a white solid.

Workup

  1. customthe resulting mixture was quenched with H2O
  2. extractionextracted with EtOAc (2 x)
  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-6562da405fb74e89954758427d45f1ab
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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