Thionyl Chloride → HCID 86596397, compound

HRID 492172Notes

Reaction equation

HRID 492172 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)[CH:20]=[CH:19][N: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)[CH:20]=[CH:19][N:18]=2)[CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689705511-(Isoquinolin-1-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596397HCID 86596397, compound

Procedure

35 cm3 of thionyl chloride are added at 25° C. under an argon atmosphere to 1.2 g (4 mmol) of 3-carboxy-1-(isoquinol-1-yl)-1H-indole. After stirring at reflux for 4 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 1.3 g of 3-chlorocarbonyl-1-(isoquinol-1-yl)-1H-indole hydrochloride in the form of a pale yellow solid which is used directly in the following step.

Workup

  1. temperatureat reflux for 4 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-a9d6b1cbe4524939b5373935b6fc3fea
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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