Thionyl Chloride → 6-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carbonyl chloride

HRID 492203Notes

Reaction equation

HRID 492203 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[N:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:5]=1)(O)=[O:2].S(Cl)([Cl:27])=O>CN(C)C=O>[Cl:27][C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[N:6]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH:5]=1)=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 689717576-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 713779096-Methoxy-1-(quinolin-4-yl)-1H-indole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

30 cm3 of sulphinyl chloride and one drop of dimethylformamide are added, at a temperature in the region of 22° C. and under an argon atmosphere, to 2.4 g (7.52 mmol) of 3-carboxy-6-methoxy-1-(quinol-4-yl)-1H-indole. After stirring at reflux for 16 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give 2.5 g of 3-chlorocarbonyl-6-methoxy-1-(quinol-4-yl)-1H-indole in the form of a yellow solid which is used directly in the following step.

Workup

  1. temperatureat reflux for 16 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-bcadf2f98f964997b184d9ab6d5f3460
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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