Phosphorus oxychloride → 2-Chloro-3-quinolinecarboxaldehyde

HRID 2413146Notes

Reaction equation

HRID 2413146 reaction equation
[Cl:1][C:2]1[C:11]([C:12]#N)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.P(Cl)(Cl)(Cl)=[O:15]>CN(C)C=O>[Cl:1][C:2]1[C:11]([CH:12]=[O:15])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 115646012-Chloroquinoline-3-carbonitrile

Product 1

HCID 6909582-Chloro-3-quinolinecarboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Where the starting material above is a 2-chloro-3-cyanoquinoline, this can be prepared by starting from an appropriate substituted acetanilide. This is heated with phosphoryl chloride and dimethylformamide to give the corresponding 2-chloro-3-quinolinecarboxaldehyde. The process involved is discussed in detail by meth-Cohn et al., J. Chem. Soc., Perkin Trans. 1, 1981, 1520. The chloroquinolinecarboxaldehyde is then reacted with hydroxylamine hydrochloride, formic acid and sodium formate with heating to give the corresponding 3-cyano-2(1H)-quinolinone. This is then heated with an excess of phosphoryl chloride to give the desired 2-chloro-3-cyanoquinoline.

Workup

  1. customthis can be prepared

Sources & evidence

ORD record
ord-c7af54f1350c4003bb68443f5af61e78
Source dataset
uspto-grants-1985_01
Patent number
US04496569

Reaction notes

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