Thionyl Chloride → HCID 86596405, compound

HRID 492184Notes

Reaction equation

HRID 492184 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=2)[N:10]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:9]=1)(O)=[O:6]>>[ClH:3].[Cl:3][C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH3:17])[CH:15]=2)[N:10]([C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689687275-Methyl-1-(quinolin-2-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596405HCID 86596405, compound

Procedure

15 cm3 of thionyl chloride are added at 22° C. under an argon atmosphere to 0.95 g (2.70 mmol) of 3-carboxy-5-methyl-1-(quinol-2-yl)-1H-indole. After stirring at reflux for 3.5 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), successively triturated twice with 10 cm3 of dimethoxyethane and then concentrated to dryness under reduced pressure (2.7 kPa) to give 1 g of 3-chlorocarbonyl-5-methyl-1-(quinol-2-yl)-1H-indole hydrochloride in the form of a yellow solid which is used directly in the following step.

Workup

  1. temperatureat reflux for 3.5 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customsuccessively triturated twice with 10 cm3 of dimethoxyethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-323812b4f7934ccaad4366d2a541b4df
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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