Hydrochloric Acid → HCID 18958809, compound

HRID 1708370Notes

Reaction equation

[ClH:1].[CH2:2]([N:4]([CH2:17][CH3:18])[CH:5]1[CH2:14][C:13]2[C:8](=[C:9]([CH3:15])[CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]1=[O:16])[CH3:3].[H-].[Na+].[CH3:21]I.Cl>CN(C)C=O.O>[ClH:1].[CH3:21][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][C:9]=2[CH3:15])[CH2:14][CH:5]([N:4]([CH2:2][CH3:3])[CH2:17][CH3:18])[C:6]1=[O:16]

Participants

Conditions

Temperature: 50 °C

Procedure

Solution of 12.3 g of 3-diethylamino-8-methyl-3,4-dihydrocarbostyril hydrochloride in 100 ml of anhydrous dimethylformamide was added 1.9 g of 60%-sodium hydride, then this mixture was heated at 50° C. for 30 minutes. Next, to this reaction mixture was added dropwise 6.53 g of methyl iodide under ice-cooling condition. After the dropwise addition, the whole mixture was heated at 50° to 60° C. with stirring. The reaction mixture was poured in water, and was extracted with chloroform. The chloroform layer was washed with water, and dried. Chloroform was removed by evaporation, and the residue thus obtained was converted into a hydrochloride, and recrystallized from acetone-n-hexane to obtain 12 g of 1-methyl-3-diethylamino-8-methyl-3,4-dihydrocarbostyril hydrochloride. Light brown powdery substance. Melting point: 162.5°-164.5° C.

Workup

temperaturecooling condition
additionAfter the dropwise addition
temperaturethe whole mixture was heated at 50° to 60° C.
extractionwas extracted with chloroform
washThe chloroform layer was washed with water
customdried
customChloroform was removed by evaporation
customthe residue thus obtained
customrecrystallized from acetone-n-hexane

Sources & evidence

ORD record: ord-4bea98de917b4ecd8f104a91421eca8b
Source dataset: uspto-grants-1994_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05358949

Reaction notes

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