Phosphorus oxychloride → 4-Chloroquinoline

HRID 983885Notes

Reaction equation

HRID 983885 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516385quinolin-4-ol

Product 1

HCID 691404-Chloroquinoline

Procedure

In this scheme, the ethyl ester (A1) is condensed with the appropriate aniline (A2), in the presence of acid, to form an imine. The imine is then cyclized by heating at about 260-280° C. to give the corresponding 4-hydroxyquinoline (A3). The 4-hydroxyquinoline (A3) is subsequently refluxed with phosphorous oxychloride to form a 4-chloroquinoline (A4).

Sources & evidence

ORD record
ord-992e4ca67ad14daa942f7b8c9204d3bc
Source dataset
uspto-grants-2005_03
Patent number
US06867185B2

Reaction notes

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