Diethyl (ethoxymethylene)malonate → ethyl 6,7-dihydro-9-(N,N-dimethylamino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate

HRID 1287874

Reaction equation

[CH3:1][N:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]([CH3:14])[CH2:8][CH2:7]2)[CH3:3].C([O:17][CH:18]=[C:19]([C:25](OCC)=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21])C.[OH-].[Na+]>O>[CH3:3][N:2]([C:4]1[CH:13]=[C:12]2[C:11]3[N:10]([CH:25]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18]2=[O:17])[CH:9]([CH3:14])[CH2:8][CH2:7][C:6]=3[CH:5]=1)[CH3:1]

Participants

Conditions

Temperature: 120 °C

Procedure

6-(N,N-Dimethylamino)-2-methyltetrahydroquinoline (25 g., 0.132 mole) is mixed with diethyl ethoxymethylenemalonate (28.4 g., 0.132 mole), and the mixture is heated at 120° C. for 3 hours. Polyphosphoric acid (200 g.) is added, and the solution is heated gradually to 120° C. with occasional stirring. The solution is maintained at 120° to 130° C. for 1 hour then poured into 500 ml. of water, with stirring. The solution is neutralized with 40 percent sodium hydroxide solution. The yellow product is separated by filtration and recrystallized from ethanol giving ethyl 6,7-dihydro-9-(N,N-dimethylamino)-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylate, m.p. 219°-222° C.

Workup

temperaturethe solution is heated gradually to 120° C. with occasional stirring
temperatureThe solution is maintained at 120° to 130° C. for 1 hour
additionthen poured into 500 ml
customThe yellow product is separated by filtration
customrecrystallized from ethanol

Sources & evidence

ORD record: ord-9102ee7178db4b24afd8420af9232718
Source dataset: uspto-grants-1976_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03985882

Linked notes

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