HCID 13094348, compound → HCID 13094340, compound

HRID 1285207Notes

Reaction equation

HRID 1285207 reaction equation
C([C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][CH2:8][CH:9]([CH3:20])[N:10]3[C:15]=2[C:14]=1[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11]3)#N.NC1C=CC2CCC(C)N3C=2C=1C(=O)C(C(O)=O)=C3>>[CH3:20][CH:9]1[N:10]2[C:15]3[C:14](=[CH:3][CH:4]=[CH:5][C:6]=3[CH2:7][CH2:8]1)[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11]2

Participants

3

Reactant 2

HCID 13094348HCID 13094348, compoundHCID 13094356HCID 13094356, compound

Product 1

HCID 13094340HCID 13094340, compound

Procedure

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.

Sources & evidence

ORD record
ord-27c99bfa607f45dc82cb7e5c0eee2b4f
Source dataset
uspto-grants-1986_01
Patent number
US04565872

Reaction notes

Loading…