Thionyl Chloride → HCID 86596417, compound

HRID 492214Notes

Reaction equation

HRID 492214 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[N:10]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)[CH:9]=1)([OH:7])=O>CN(C)C=O>[ClH:3].[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:18]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=1)[CH:9]=[C:8]2[C:5]([Cl:3])=[O:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 689703725-Chloro-1-(quinolin-4-yl)-1H-indole-3-carboxylic acid

Product 1

HCID 86596417HCID 86596417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

45 cm3 of sulphinyl chloride and one drop of dimethylformamide are added to 2.1 g (6.51 mmol) of 3-carboxy-5-chloro-1-(quinolin-4-yl)-1H-indole at a temperature in the region of 20° C. under an argon atmosphere. After stirring at reflux for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), giving 2.5 g of 5-chloro-3-chlorocarbonyl-1-(quinolin-4-yl)-1H-indole hydrochloride in the form of a cream-colored solid, which is used directly in the following step.

Workup

  1. temperatureat reflux for 1 hour
  2. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-f80f45f392ae425aa1fe1393de1a7d3c
Source dataset
uspto-grants-2009_05
Patent number
US07531663B2

Reaction notes

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