Acetone → HCID 18958779, compound

HRID 1708368Notes

Reaction equation

HRID 1708368 reaction equation
Cl.[NH2:2][CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14].[CH2:15](I)[CH3:16].C(=O)([O-])[O-].[K+].[K+].[Cl:24]CCl.O.[CH3:28][C:29](C)=O>>[ClH:24].[CH2:28]([N:2]([CH2:15][CH3:16])[CH:3]1[CH2:12][C:11]2[C:6](=[C:7]([CH3:13])[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:14])[CH3:29]

Participants

6

Reactant 5

HCID 180AcetoneHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14627260HCID 14627260, compoundHCID 21908982Water methylene chloride

Product 1

HCID 18958779HCID 18958779, compound

Conditions

Temperature
120 °C

Procedure

1.6 Grams of 3-amino-8-methyl-3,4-dihydrocarbostyril hydrochloride was suspended in 30 ml of acetone, then 2.6 g of ethyl iodide and 2.6 g of potassium carbonate were added thereto, next the mixture was placed in a sealed tube and reacted by heating at 120° C. for 10 hours. To the reaction mixture, was added dichloromethane-water, and the organic layer was collected by separation. The organic layer was washed with water, then dried with anhydrous sodium sulfate. The solvent was removed by evaporation, then the residue thus obtained was purified by a silica gel column chromatography (eluent: dichloromethane:methanol=100:1). Recrystallized from ethanol-diethyl ether to obtain 1.5 g of 3-diethylamino-8-methyl-3,4-dihydrocarbostyril hydrochloride. White powdery substance. Melting point: 231.5°-233° C.

Workup

  1. customnext the mixture was placed in a sealed tube
  2. customreacted
  3. customthe organic layer was collected by separation
  4. washThe organic layer was washed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue thus obtained
  8. customwas purified by a silica gel column chromatography (eluent: dichloromethane:methanol=100:1)
  9. customRecrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-c109781f6ebe4109aa2650851fb78daf
Source dataset
uspto-grants-1994_10
Patent number
US05358949

Reaction notes

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