Sodium Hydroxide → HCID 15632080, compound

HRID 48916Notes

Reaction equation

HRID 48916 reaction equation
[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[CH:5][CH:4]=[C:3]1[C:12]([O:14]CC)=[O:13].[OH-].[Na+]>CO>[O:1]=[C:2]1[N:11]2[C:6]([CH:7]=[CH:8][CH:9]=[CH:10]2)=[CH:5][CH:4]=[C:3]1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 4615166Ethyl 4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 15632080HCID 15632080, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 4-oxo-4H-quinolizine-3-carboxylate (1) (100 mg, 0.46 mmol) in 4 ml methanol was added 300 μl NaOH (3 M). The reaction mixture was stirred overnight, followed by evaporation of the solvent in vacuo. The remaining solid was dissolved in 4 ml water and the clear solution was acidified to pH 1, with 1 M HCl. The resulting suspension was filtered, and the residue was dried in vacuo over P2O5 to give yellow plates of 4-oxo-4H-quinolizine-3-carboxylic acid (1a) (63 mg, 72%). M.p. 235-240° C. 1H NMR (δ, DMSO-d6): 7.26 (d, J=8 Hz, 1H), 7.64 (dd, J=7 Hz, J=7 Hz, 1H), 8.03 (dd, J=7 Hz, J=7 Hz, 1H), 8.14 (d, J=9 Hz, 1H), 8.39 (d, J=9 Hz, 1H), 9.27 (d, J=7 Hz), 14.13 (s, 1H). MS: m/z 189.0433; required for C12H11NO3: 189.0428.

Workup

  1. customfollowed by evaporation of the solvent in vacuo
  2. dissolutionThe remaining solid was dissolved in 4 ml water
  3. filtrationThe resulting suspension was filtered
  4. dry with materialthe residue was dried in vacuo over P2O5

Sources & evidence

ORD record
ord-2c4dfb91e55c4427b8dd24905a3bbd4b
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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