Sulfuric Acid → HCID 69680015, compound

HRID 1369928Notes

Reaction equation

HRID 1369928 reaction equation
C[O:2][C:3]([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:4].[OH-].[Na+].S(=O)(=O)(O)O>C1COCC1.CO>[C:3]([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)([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 18516355HCID 18516355, compound

Product 1

HCID 69680015HCID 69680015, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.0 g (14.6 mmol) of 7-(2-methoxycarbonylethyl)-1,2,3,3a,5,9b-hexahydro-cyclopenta[c]quinolin-4-one in 60 ml of THF and 100 ml of methanol is stirred for 24 hours with 29 ml of 1 M aqueous sodium hydroxide solution. The batch is set at pH 5 with 10% sulfuric acid and extracted with dichloromethane and ethyl acetate. The combined extracts are freeze-dried (Na2SO4) and concentrated by evaporation in a vacuum. After column chromatography on silica gel with dichloromethane-methanol, 3.4 g of 7-(carboxyethyl)-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one is isolated.

Workup

  1. extractionextracted with dichloromethane and ethyl acetate
  2. dry with materialThe combined extracts are freeze-dried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-9438273f4b7245129507aeb699760a9a
Source dataset
uspto-grants-2003_06
Patent number
US06579883B1

Reaction notes

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