Thionyl Chloride → HCID 86596408, compound

HRID 492187Notes

Reaction equation

HRID 492187 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[N:6]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:5]=1)(O)=[O:2].S(Cl)([Cl:26])=O>>[ClH:26].[Cl:26][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:13])[CH:11]=2)[N:6]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:5]=1)=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689687005-Methyl-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596408HCID 86596408, compound

Procedure

10 cm3 of thionyl chloride are added at 22° C. under an argon atmosphere to 1 g (3 mmol) of 3-carboxy-5-methyl-1-(quinol-4-yl)-1H-indole. After stirring at reflux for 2.5 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), successively triturated twice with 5 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-4-yl)-1H-indole hydrochloride in the form of a yellow solid which is used directly in the following step.

Workup

  1. temperatureat reflux for 2.5 hours
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  3. customsuccessively triturated twice with 5 cm3 of dimethoxyethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-adb88a2657a7400094bff5f93fd34f19
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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