Sodium Bicarbonate → Ethyl 1-butyryl-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate

HRID 598112Notes

Reaction equation

C(O[CH:4]([CH:26]([C:32](OCC)=[O:33])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:5]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:12]=1)[C:6](=[O:10])[CH2:7][CH2:8][CH3:9])C.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[C:6]([C:5]1[CH:4]=[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:32](=[O:33])[N:12]2[C:11]=1[CH:16]=[CH:15][CH:14]=[C:13]2[C:17]1[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=1[CH3:23])(=[O:10])[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

Diethyl [1-ethoxy-2-(6-mesitylpyridin-2-yl)-3-oxohexyl]malonate (0.045 g, 0.10 mmol) was dissolved in acetic acid (3 mL). The reaction was heated at 100° C. for 20 minutes. Acetic acid was stripped off via rotavap. Saturated sodium bicarbonate was added and the solution was extracted with ethyl acetate. The organics were dried, concentrated, and flash chromatographed (20% ethyl acetate/hexanes) to give 0.015 g (37% yield) of the title compound.

Workup

extractionthe solution was extracted with ethyl acetate
customThe organics were dried
concentrationconcentrated
customflash chromatographed (20% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-3cff8fcd664f4456a426df907aed3c30
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

Loading…