Oxalyl chloride → HCID 22024947, compound

HRID 1792799Notes

Reaction equation

HRID 1792799 reaction equation
C(Cl)(=O)C([Cl:4])=O.[ClH:7].[C:8]([C:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[CH:12]=1)(O)=[O:9]>ClCCl>[ClH:4].[Cl:7][C:8]([C:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[CH:12]=1)=[O:9]

Participants

4

Reactant 2

HCID 65578Oxalyl chloride2×HCID 22024962HCID 22024962, compound

Product 1

HCID 22024947HCID 22024947, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22 °C

Procedure

0.45 mL (5.16 mmol) of oxalyl chloride is added to a solution, cooled to a temperature in the region of 5° C., of 0.45 g (1.64 mmol) of 3-carboxy-1-(quinol-8-yl)-1H-pyrrole hydrochloride in 20 mL of dichloromethane under an argon atmosphere. After stirring at a temperature in the region of 22° C. for 15 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa), then it is placed under an argon atmosphere and 20 mL of dichloromethane and 0.45 mL (5.16 mmol) of oxalyl chloride are successively added. After stirring at a temperature in the region of 22° C. for 15 hours, concentrating the reaction medium to dryness under reduced pressure (2.7 kPa) gives 0.418 g of 3-chlorocarbonyl-1-(quinol-8-yl)-1H-pyrrole hydrochloride in the form of a cream-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. stirringAfter stirring at a temperature in the region of 22° C. for 15 hours
  3. concentrationconcentrating the reaction medium to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-53e910dc6ecf4007b8f1e9f0503f1f12
Source dataset
uspto-grants-2006_07
Patent number
US07078414B2

Reaction notes

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