Sodium Cyanide → 6-Hydroxy-3-quinolinecarbonitrile

HRID 2222302Notes

Reaction equation

HRID 2222302 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2.[C-:13]#[N:14].[Na+].[Cl-].[NH4+]>CN1CCCC1=O.O>[C:13]([C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([OH:12])=[CH:7][CH:6]=2)#[N:14]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 148078713-Bromoquinolin-6-ol

Product 1

HCID 219231416-Hydroxy-3-quinolinecarbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

3-Bromo-6-hydroxyquinoline (1.12 g) in dry N-methylpyrrolidin-2-one (10 ml) was treated with cuprous cyanide (0.55 g) and stirred at 150° C. for 7 hours under an atmosphere of nitrogen then stored at ambient temperature for 18 hours. The mixture was treated with sodium cyanide (1.5 g) in water (5 ml) and heated at 75° C. for 15 minutes. 10% Aqueous ammonium chloride solution (25 ml) was added and the mixture cooled to ambient temperature. The reaction mixture was extracted with ethyl acetate and the organic phase separated, washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give a yellow brown solid. The solid was fractionated by chromatography to give the required product as a yellow solid.

Workup

  1. waitthen stored at ambient temperature for 18 hours
  2. temperatureheated at 75° C. for 15 minutes
  3. temperaturethe mixture cooled to ambient temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. customthe organic phase separated
  6. washwashed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated under reduced pressure
  9. customto give a yellow brown solid

Sources & evidence

ORD record
ord-9eede1a3f0ff474aab195bf000d3a205
Source dataset
uspto-grants-2008_05
Patent number
US07371764B2

Reaction notes

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