Sodium Hydroxide → 4-Chloroquinoline-6-carbonitrile

HRID 1699894Notes

Reaction equation

HRID 1699894 reaction equation
P(Cl)(Cl)([Cl:3])=O.O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1.[OH-].[Na+]>CN(C=O)C>[Cl:3][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[N:18])[CH:15]=2)[N:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 116583514-Hydroxyquinoline-6-carbonitrile

Product 1

HCID 204935814-Chloroquinoline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus oxychloride (0.518 ml) was added to DMF (9 ml) at an inner temperature of 5-7° C. while stirring under ice-cooling, and the mixture was stirred at room temperature for 0.5 hr. 4-Hydroxy-6-quinolinecarbonitrile (860 mg) was added while stirring under ice-cooling and the mixture was stirred under ice-cooling for 1 hr. 1N aqueous sodium hydroxide solution (18 ml) was added and the mixture was stirred at room temperature for 10 min. The precipitate was collected by filtration and washed with water to give a pale brown powder. The obtained powder was purified by silica gel column chromatography (eluent: chloroform-methanol=50/1) to give the object compound (800 mg) as a pale yellow powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 0.5 hr
  3. stirringwhile stirring under ice-
  4. temperaturecooling
  5. stirringthe mixture was stirred under ice-
  6. temperaturecooling for 1 hr
  7. stirringthe mixture was stirred at room temperature for 10 min
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with water
  10. customto give a pale brown powder
  11. customThe obtained powder was purified by silica gel column chromatography (eluent: chloroform-methanol=50/1)

Sources & evidence

ORD record
ord-cd062ac97a03475aa167a791cdbcde0d
Source dataset
uspto-grants-2002_02
Patent number
US06348474B1

Reaction notes

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