Oxalyl chloride → HCID 86596415, compound
Reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].C(C1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[N:20]=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=1)(O)=O>ClCCl>[ClH:4].[Cl:4][C:2]([C:1]1[C:14]2[C:13](=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:12]([C:19]2[N:20]=[CH:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:11]=1)=[O:3]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 22 °C
Procedure
0.7 cm3 (8 mmol) of oxalyl chloride is added to a suspension, cooled to a temperature in the region of 5° C., of 0.74 g (2.57 mmol) of 3-carboxy-1-(isoquinol-3-yl)-1H-indole in 15 cm3 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). The residue, dissolved in 15 cm3 of dichloromethane, is again reacted with 1 cm3 (11.46 mmol) of oxalyl chloride. After stirring at a temperature in the region of 22° C. for 48 hours, the reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) to give 0.7 g of 3-chlorocarbonyl-1-(isoquinol-3-yl)-1H-indole hydrochloride in the form of a yellow solid which is used directly in the following step.
Workup
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
- dissolutionThe residue, dissolved in 15 cm3 of dichloromethane
- stirringAfter stirring at a temperature in the region of 22° C. for 48 hours
- concentrationthe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
Sources & evidence
- ORD record
- ord-c20c21c92a734c868e84b994c10a1e0e
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07531663B2
Reaction notes
Loading…