Dichloromethane → HCID 19696421, compound

HRID 863707Notes

Reaction equation

HRID 863707 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=O.[C:7]([O:10][CH2:11][CH:12]1[CH2:24][CH2:23][N:15]2[C:16]3[C:21]([CH:22]=[C:14]2[CH2:13]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:9])[CH3:8].Cl[CH2:26][Cl:27]>>[C:7]([O:10][CH2:11][CH:12]1[CH2:24][CH2:23][N:15]2[C:16]3[C:21]([C:22]([C:8]4[C:7](=[O:9])[O:10][C:1](=[O:5])[C:2]=4[C:23]4[CH:24]=[CH:12][CH:13]=[CH:14][C:26]=4[Cl:27])=[C:14]2[CH2:13]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:9])[CH3:8]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 14954045HCID 14954045, compound

Product 1

HCID 19696421HCID 19696421, compound

Procedure

2.2 g of oxalyl chloride were added to an ice-cold solution of 4 g of 8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indole in 50 ml of dichloromethane. After 2 hours, the solvent was evaporated and the residue was dissolved in dichloromethane. This solution was added to a solution of 3.0 g of 2-chlorophenylacetic acid and 4.0 g of triethylamine in dichloromethane. The mixture was stirred for 16 hours and then concentrated. Chromatography of the residue on silica gel with dichloromethane/methanol (95:5) yielded 0.9 g of 3-[8-(acetoxymethyl)-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-(2-chlorophenyl)furan-2,5-dione of melting point 168°-171° C.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. additionThis solution was added to a solution of 3.0 g of 2-chlorophenylacetic acid and 4.0 g of triethylamine in dichloromethane
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8f26b6536ef144dc87c338f24977838b
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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