Thionyl Chloride → HCID 86596403, compound

HRID 492181Notes

Reaction equation

HRID 492181 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[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][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[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][N:19]=2)[CH:9]=1)=[O:6]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689714021-(Isoquinolin-1-yl)-5-methyl-1H-indole-3-carboxylic acid

Product 1

HCID 86596403HCID 86596403, compound

Procedure

15 cm3 of thionyl chloride are added at 20° C. under an argon atmosphere to 1.27 g (3.75 mmol) of 3-carboxy-1-(isoquinol-1-yl)-5-methyl-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 1.2 g of 3-chlorocarbonyl-1-(isoquinol-1-yl)-5-methyl-1H-indole hydrochloride in the form of a 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-6eb6bee652024121803b7be2209f12be
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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