Thionyl Chloride → HCID 86596399, compound

HRID 492175Notes

Reaction equation

HRID 492175 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=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]=[CH:14][CH:15]=2)[N:10]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=[CH:19][CH:18]=2)[CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689726591-(Quinolin-4-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596399HCID 86596399, compound

Procedure

25 cm3 of thionyl chloride are added at 25° C. under an argon atmosphere to 0.85 g (2.6 mmol) of 3-carboxy-1-(quinol-4-yl)-1H-indole. After stirring at reflux for 3 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 0.9 g of 3-chlorocarbonyl-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 3 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-686015e3e016440fb8946f5ac018200e
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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