Oxalyl chloride → HCID 22024988, compound

HRID 1792786Notes

Reaction equation

HRID 1792786 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C([C:10]1[CH:14]=[CH:13][N:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[C:11]=1C)(O)=O>ClCCl>[ClH:4].[Cl:4][C:2]([C:1]1[CH:10]=[CH:11][N:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[CH:17][CH:16]=2)[C:13]=1[CH3:14])=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 220249512-Methyl-1-(quinolin-4-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 22024988HCID 22024988, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

11.8 mL (134.8 mmol) of oxalyl chloride are added at 20° C. under an argon atmosphere to 2.09 g (7.24 mmol) of 3-carboxy-2-methyl-1-(quinol-4-yl)-1H-pyrrole dissolved in 150 mL of dichloromethane. After stirring at 20° C. for 16 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give 2.2 g of 3-chlorocarbonyl-2-methyl-1-(quinol-4-yl)-1H-pyrrole hydrochloride in the form of an orange-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)

Sources & evidence

ORD record
ord-0fdfc446bfd34bf9ba01fbb53c5b1065
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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