Oxalyl chloride → HCID 22024994, compound

HRID 1792797Notes

Reaction equation

HRID 1792797 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C([C:10]1C=[CH:13][N:12]([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH:11]=1)(O)=O>ClCCl>[ClH:4].[Cl:4][C:2]([C:1]1[CH:10]=[CH:11][N:12]([C:15]2[CH:24]=[CH:23][CH:22]=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[N:20]3)[CH:13]=1)=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 220249671-(Quinolin-5-yl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 22024994HCID 22024994, compoundYield 106.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

0.5 mL (5.73 mmol) of oxalyl chloride is added to a solution, cooled to a temperature in the region of 5° C., of 0.42 g (1.76 mmol) of 3-carboxy-1-(quinol-5-yl)-1H-pyrrole in 10 mL of dichloromethane under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 15 hours, concentrating the reaction mixture to dryness under reduced pressure (2.7 kPa) gives 0.55 g of 3-chlorocarbonyl-1-(quinol-5-yl)-1H-pyrrole hydrochloride in the form of a cream-coloured solid which is used directly in the following step.

Workup

  1. concentrationconcentrating the reaction mixture to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-9c1ae5b007ce40f89648f68658dddefe
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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