Thionyl Chloride → HCID 86596411, compound

HRID 492194Notes

Reaction equation

HRID 492194 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH:5]=1)(O)=[O:2].S(Cl)([Cl:25])=O>>[ClH:25].[Cl:25][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]=[CH:18][CH:17]=[CH:16]3)[CH:5]=1)=[O:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 689685141-(Quinolin-6-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596411HCID 86596411, compound

Procedure

20 cm3 of thionyl chloride are added at 22° C. under an argon atmosphere to 0.69 g (2.1 mmol) of 3-carboxy-1-(quinol-6-yl)-1H-indole. After stirring at reflux for 4 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is 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-1-(quinol-6-yl)-1H-indole hydrochloride in the form of an orange-coloured 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. customThe residue is successively triturated twice with 10 cm3 of dimethoxyethane
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-58353114c3a446408dac349b47561391
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

Loading…