Diethyl (ethoxymethylene)malonate → 9-acetamido-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
Reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([CH3:15])[CH:9]=[C:8]2Cl)(=[O:3])[CH3:2].C(NC1C=C2C(=CC=1)NC(C)CC2)(=O)C.N1C2C(=CC=CC=2)CCC1.C([O:44][CH:45]=[C:46]([C:52](OCC)=O)[C:47]([O:49]CC)=[O:48])C.NC1C=C2C3N(C=C(C(O)=O)C2=O)C(C)CCC=3C=1.C(OC(=O)C)(=O)C>>[C:1]([NH:4][C:5]1[CH:14]=[C:13]2[C:12]3[N:11]([CH:52]=[C:46]([C:47]([OH:49])=[O:48])[C:45]2=[O:44])[CH:10]([CH3:15])[CH2:9][CH2:8][C:7]=3[CH:6]=1)(=[O:3])[CH3:2]Participants
Reactant 6
HCID 6871Diethyl (ethoxymethylene)malonate
HCID 7918Acetic Anhydride
HCID 694601,2,3,4-Tetrahydroquinoline
HCID 227603N-(4-chloro-2-methyl-6-quinolyl)acetamide
HCID 130943579-amino-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
HCID 214453586-Acetamido-2-methyl-1,2,3,4-tetrahydroquinolineProduct 1
Conditions
- Temperature
- 140 °C
Procedure
6-Acetamido-4-chloro-2-methylquinoline is reduced catalytically to the novel compound 6-acetamido-2-methyl-1,2,3,4-tetrahydroquinoline. The tetrahydroquinoline is condensed with diethyl ethoxymethylenemalonate by heating without a solvent for one hour at 140° C. Polyphosphoric acid is added, and the solution is heated at 100° C. for one-half hour. The product, 9-amino-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid is reacted with acetic anhydride as described in Example 49 to provide 9-acetamido-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. >310° C. The product is characterized by spectral analysis and elemental analysis, which are found to be consistent with the indicated structure.
Workup
- temperaturethe solution is heated at 100° C. for one-half hour
Sources & evidence
- ORD record
- ord-dca999f0e8ad4fe7a9c8656108403fb2
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04014877
Reaction notes
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