Diethyl (ethoxymethylene)malonate → HCID 15592450, compound
Reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:16][CH:17]1[CH2:26][CH2:25][C:24]2[C:23]3[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=3[CH:21]=[CH:20][C:19]=2[NH:18]1>O>[CH3:16][CH:17]1[CH2:26][CH2:25][C:24]2=[C:23]3[C:22](=[CH:21][C:20]4=[C:19]2[N:18]1[CH2:4][CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]4=[O:13])[CH:30]=[CH:29][CH:28]=[CH:27]3Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 200 °C
Procedure
A mixture of diethyl ethoxymethylenemalonate (17.3 g., 0.08 mole) and 3-methyl-1,2,3,4-tetrahydrobenzo[f]quinoline (prepared by reduction of 1-chloro-3-methylbenzo[f]quinoline with rhodium on carbon) (15.8 g., 0.08 mole) was heated to 200° C., then slowly cooled to about 170° C. and maintained at that temperature for about three hours. After cooling to ambient temperature, polyphosphoric acid (100 g.) was added and the mixture was heated at 90° C. with manual stirring. The temperature was permitted to rise gradually to about 110° C. and the mixture was observed to foam. After the foam subsided, the mixture was poured into hot water with stirring. An oil formed which became a yellow solid when cooled. Recrystallization from methanol provided ethyl 1,2-dihydro-3-methyl-7-oxo-3H,5H-naphtho[1,2,3-ij]quinolizine-6-carboxylate as a pale yellow solid, m.p. 178°-180° C.
Workup
- temperatureslowly cooled to about 170° C.
- temperaturemaintained at that temperature for about three hours
- temperatureAfter cooling to ambient temperature
- temperaturethe mixture was heated at 90° C. with manual stirring
- customto rise gradually to about 110° C.
- customAn oil formed which
- temperaturecooled
- customRecrystallization from methanol
Sources & evidence
- ORD record
- ord-9b3665628cbd4d869cfb684d8097222c
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04456606
Reaction notes
Loading…