Ethanol → HCID 86740276, compound

HRID 485829Notes

Reaction equation

Cl.Cl[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([C:14](=[O:16])[CH3:15])([NH2:13])[N:10]([CH3:17])[CH2:9][CH:8]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1.C(O)C.[CH2:28]([NH2:30])[CH3:29].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]\[C:34]([OH:36])=[O:35]>CCOCC>[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]\[C:34]([OH:36])=[O:35].[CH2:28]([NH:30][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[C:11]([C:14](=[O:16])[CH3:15])([NH2:13])[N:10]([CH3:17])[CH2:9][CH:8]2[C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)[CH3:29]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5.2 g (0.0145 mole) of 8-chloro-acetyl-amino-2-methyl-4-p-tolyl-1,2,3,4-tetrahydro-isoquinoline-hydrochloride, 100 ml of ethanol and 30 ml (20.8 g, 0.45 mole) of ethyl amine is heated in a bomb tube at 70° C. for 5 hours. The reaction mixture is evaporated, the residual orange oil is dissolved in 50 ml of ethanol and reacted with 1.8 g (0.0155 mole) of maleic acid. The solution is diluted with 150 ml of ether in portions, cooled, and the precipitated product is filtered off and washed with a mixture of acetone and ether. The product 5.7 g, [white powder, mp.: 157° C. (decomposition)] is recrystallized from a mixture of ethanol and ether. Thus 4.3 g of the title compound are obtained. Yield 66%, mp.: 176° C. (decomposition).

Workup

customThe reaction mixture is evaporated
dissolutionthe residual orange oil is dissolved in 50 ml of ethanol
temperaturecooled
filtrationthe precipitated product is filtered off
washwashed with a mixture of acetone and ether
customThe product 5.7 g, [white powder, mp.: 157° C. (decomposition)] is recrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record: ord-b732d541adc94abe9b55c3d869b8198b
Source dataset: uspto-grants-1985_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04537895

Reaction notes

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