8,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester → 8,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 2413962Notes

Reaction equation

HRID 2413962 reaction equation
C([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([Cl:21])=[C:19]([Cl:20])[C:12]3=[C:13]2[N:8]([CH:9]([CH3:23])[CH2:10][C:11]3=[O:22])[CH:7]=1)=[O:5])C>Cl.C(O)(=O)C>[Cl:20][C:19]1[C:12]2=[C:13]3[N:8]([CH:9]([CH3:23])[CH2:10][C:11]2=[O:22])[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:15](=[O:16])[C:14]3=[CH:17][C:18]=1[Cl:21]

Participants

4

Reactant 1

HCID 139602018,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester

Product 1

HCID 201543468,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

7.08 g (0.02 mole) of 8,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in a mixture of 14 ml of concentrated hydrochloric acid and 56 ml of acetic acid, and this suspension was stirred at 110°-120° C. for 3 hours to hydrolyze the starting material. The resulting reaction solution was allowed to cool to room temperature. The precipitate which separated out was collected by filtration and washed with water to obtain 5.61 g (86.0% yield) of 8,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid in the form of pale-yellow crystals.

Workup

  1. customThe resulting reaction solution
  2. customThe precipitate which separated out
  3. filtrationwas collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-18a7c564e47c42f7999a0a2ffd0b66a9
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

Loading…