Oxalyl chloride → HCID 22024952, compound

HRID 1792823Notes

Reaction equation

HRID 1792823 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(C1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][N:12]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][N:20]=2)[CH:11]=1)(O)=O>ClCCl>[ClH:4].[Cl:4][C:2]([C:1]1[C:14]([C:15]([F:17])([F:18])[F:16])=[CH:13][N:12]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][N:20]=2)[CH:11]=1)=[O:3]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 220249571-(Isoquinolin-1-yl)-4-(trifluoromethyl)-1H-pyrrole-3-carboxylic acid

Product 1

HCID 22024952HCID 22024952, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

0.62 mL (7.18 mmol) of oxalyl chloride is added to 1.1 g (3.59 mmol) of 3-carboxy-4-trifluoromethyl-1-(isoquinolin-1-yl)-1H-pyrrole dissolved in 30 mL of dichloromethane at a temperature in the region of 20° C. under an argon atmosphere. After stirring for 2 hours at a temperature in the region of 20° C., the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), giving 1.22 g of 3-chlorocarbonyl-4-trifluoromethyl-1-(isoquinolin-1-yl)-1H-pyrrole hydrochloride in the form of a cream-colored 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-dd8cf941d89e4753913048bb8c4aed3f
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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