Diethyl (ethoxymethylene)malonate → 6,7-dihydro-9-fluoro-1-oxo-5-trifluoromethyl-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 1287882Notes

Reaction equation

HRID 1287882 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]([F:15])([F:14])[F:13])[CH2:6][CH2:5]2.C([O:18][C:19](=[O:30])[C:20](=[CH:26]OCC)[C:21](OCC)=[O:22])C>>[F:1][C:2]1[CH:11]=[C:10]2[C:9]3[N:8]([CH:26]=[C:20]([C:19]([OH:30])=[O:18])[C:21]2=[O:22])[CH:7]([C:12]([F:13])([F:15])[F:14])[CH2:6][CH2:5][C:4]=3[CH:3]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 21445341HCID 21445341, compound

Product 1

HCID 130943696,7-dihydro-9-fluoro-1-oxo-5-trifluoromethyl-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Procedure

6-Fluoro-2-trifluoromethyltetrahydroquinoline is condensed with an equimolar amount of diethylethoxymethylenemalonate according to the method of Example 1. The ester intermediate of Formula III is hydrolyzed according to Example 1, and the solid product is recrystallized from N,N-dimethyl formamide to provide crystals of 6,7-dihydro-9-fluoro-1-oxo-5-trifluoromethyl-1H,5H-benzo[ij]quinolizine-2-carboxylic acid, m.p. 295°-297° C.

Workup

  1. customthe solid product is recrystallized from N,N-dimethyl formamide

Sources & evidence

ORD record
ord-40c5caca84c54480ad0d0e038db53014
Source dataset
uspto-grants-1976_10
Patent number
US03985882

Reaction notes

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