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

HRID 1792815Notes

Reaction equation

HRID 1792815 reaction equation
S(Cl)([Cl:3])=O.[C:5]([C:8]1[C:12]([CH:13]2[CH2:15][CH2:14]2)=[CH:11][N:10]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:9]=1)(O)=[O:6]>C(Cl)(Cl)Cl>[Cl:3][C:5]([C:8]1[C:12]([CH:13]2[CH2:15][CH2:14]2)=[CH:11][N:10]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH:9]=1)=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 220249384-Cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 220249424-Cyclopropyl-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 to 1.05 g (3.78 mmol) of 3-carboxy-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole dissolved in 20 mL of chloroform at a temperature in the region of 20° C. under an argon atmosphere. After stirring for one hour at the reflux temperature of the solvent, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa). The residue is dissolved in 20 mL of chloroform and then concentrated to dryness again, giving 1.12 g (3.78 mmol) of 3-chlorocarbonyl-4-cyclopropyl-1-(quinolin-4-yl)-1H-pyrrole in the form of a yellow 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
  3. concentrationconcentrated to dryness again

Sources & evidence

ORD record
ord-705b602f839943f78bb12ba9d6253c13
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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