HCID 13094348, compound → HCID 13094340, compound

Participants

Reaction Steps

U.S. Pat. Nos. 3,896,131 and 3,985,882 describe the synthesis of substituted benzo[ij]quinolizine-2-carboxylic acids. The synthesis of the compound 10-cyano-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid is described in Example 71 of said U.S. Pat. No. 3,896,131. That synthetic process utilizes 10-amino-6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as an intermediate, which intermediate is prepared from the corresponding 10-nitro compound. The 10-nitro compound is obtained by nitration of 6,7-dihydro-5-methyl-1-oxo-1H,5H-benzo[ij]-quinolizine-2-carboxylic acid. The 10-nitro compound is the predominant isomer obtained by such nitration. Accordingly, when preparing the 8-cyano final product, it would be desirable to employ a synthetic sequence which avoids such a nitration step.

Provenance & Evidence