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

HRID 597528Notes

Reaction equation

HRID 597528 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 crystal 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-0295c3ec57474ad89c4b628334b9f294
Source dataset
uspto-grants-1977_03
Patent number
US04014877

Reaction notes

Loading…