Chlorosuccinimide → HCID 69652744, compound

HRID 1831746Notes

Reaction equation

HRID 1831746 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:11]3[CH2:20][CH2:19][CH2:18][CH:12]3[C:13](=[O:17])[NH:14][C:15]=2[CH:16]=1)(=[O:3])[CH3:2].[Cl:21]N1C(=O)CCC1=O>CN(C=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[C:8]([Cl:21])=[CH:9][C:10]2[CH:11]3[CH2:20][CH2:19][CH2:18][CH:12]3[C:13](=[O:17])[NH:14][C:15]=2[CH:16]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 69652815HCID 69652815, compound

Product 1

HCID 69652744HCID 69652744, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 400 mg (1.5 mmol) of 7-acetoxyethyl-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one and 193 mg (1.5 mmol) of N-chlorosuccinimide in 40 ml of DMF is heated for 6 days to 100° C. The batch is poured onto ice water and extracted with ethyl acetate. The organic phase is washed with 10% sulfuric acid and water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 380 mg of product.

Workup

  1. additionThe batch is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with 10% sulfuric acid and water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-b826a4ba3aa244cc9ea92515ed00a086
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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