Thionyl Chloride → 4-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chloride

HRID 1792804Notes

Reaction equation

HRID 1792804 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:9]=1)(O)=[O:6]>C(Cl)(Cl)Cl>[Cl:3][C:5]([C:8]1[C:12]([CH3:13])=[CH:11][N:10]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][CH:15]=2)[CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 220249694-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 220249394-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carbonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10 mL (137 mmol) of sulphinyl chloride are added at a temperature in the region of 20° C. under an argon atmosphere to 1 g (3.97 mmol) of 3-carboxy-4-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform. After stirring at the reflux point of the solvent for 1 hour, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in 20 mL of chloroform and then brought back to dryness to give 1.07 g (3.97 mmol) of 3-chlorocarbonyl-4-methyl-1-(quinol-4-yl)-1H-pyrrole in the form of a beige-coloured solid which is used directly in the following step.

Workup

  1. concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. dissolutionThe residue is dissolved in 20 mL of chloroform

Sources & evidence

ORD record
ord-e3853d69d4f54b368c8fa00945753e65
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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