Ethyl 4-oxo-4H-quinolizine-3-carboxylate → 8-(1,2-Dicarboxyethyl)-4-Oxo-4H-Quinolizine-3-Carboxylic Acid

HRID 48917Notes

Reaction equation

HRID 48917 reaction equation
[C:1]([C:5]([C:16]1[CH:17]=[CH:18][N:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([C:26]([O:28]CC)=[O:27])[C:20]2=[O:31])(C(OC)=O)[CH2:6][C:7]([O:9]CC)=[O:8])([O:3]C)=[O:2].O=C1N2C(C=CC=C2)=CC=C1C(OCC)=O>>[C:1]([CH:5]([C:16]1[CH:17]=[CH:18][N:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[C:21]([C:26]([OH:28])=[O:27])[C:20]2=[O:31])[CH2:6][C:7]([OH:9])=[O:8])([OH:3])=[O:2]

Participants

3

Reactant 2

HCID 4615166Ethyl 4-oxo-4H-quinolizine-3-carboxylateHCID 20634153Ethyl 8-[1,1-dicarbomethoxy-2-carboethoxy-ethyl]-4-Oxo-4H-Quinolizine-3-Carboxylate

Product 1

HCID 99010888-(1,2-Dicarboxyethyl)-4-Oxo-4H-Quinolizine-3-Carboxylic AcidYield 48%

Procedure

Saponification of (20) was done as described for (1). After completion of the reaction, the solvent was evaporated in vacuo, and the resulting yellow solid was dissolved in water. The aqueous layer was acidified to pH 1, and extracted three times with ethyl acetate. Evaporation of the organic solvent gave 8-(1,2-dicarboxyethyl)-4-oxo-4H-quinolizine-3-carboxylic acid (20a) as a yellow solid in 48% yield. M.p. 250° C. 1H NMR (δ, DMSO-d6): 2.72-2.76 (m, 2H), 3.02-3.06 (m, 1H), 7.14 (d, J=9 Hz, 1H), 7.60 (dd, J=2 Hz, J=9 Hz, 1H), 7.99 (s, 1H), 8.34 (d, J=9 Hz, 1H), 9.20 (d, J=9 Hz, 1H). MS: m/z 261.0601 (M-CO2); required for C13H11NO5: 261.0637.

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe resulting yellow solid was dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-2e57e4cc3a564ca68a8620db35c20cbe
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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