Indole → 3-Chloroquinoline

HRID 1196553Notes

Reaction equation

HRID 1196553 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH-].[Na+].[CH:12]([Cl:15])(Cl)Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[Cl:15][C:12]1[CH:2]=[N:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

5

Reactant 3

HCID 798IndoleHCID 6212ChloroformHCID 14798Sodium Hydroxide

Product 1

HCID 691643-Chloroquinoline

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Procedure

Indole (ex Aldrich) was reacted with chloroform and aqueous sodium hydroxide in the presence of triethylbenzyl ammonium chloride to give 3-chloroquinoline (cf. Sundo et al, Synthesis, 4, 249 (1976). The latter was converted to 2,3-dichloroquinoline, as for Example VII.

Sources & evidence

ORD record
ord-da0338e5eb1849c4820c4b306b4d2b38
Source dataset
uspto-grants-1992_05
Patent number
US05114940

Reaction notes

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