Acetic Acid → HCID 20634148, compound

HRID 48908Notes

Reaction equation

HRID 48908 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)=O.C(O)(=O)C.[C:23]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C1C=CC=CC=1>[C:23]([C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:1][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:6](=[O:13])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]2)([O:31][CH2:32][CH3:33])=[O:30]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7761Diethyl MalonateHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate

Product 1

HCID 20634148HCID 20634148, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 100 ml round-bottom flask equipped with a Dean-Stark trap was charged with 50 ml benzene, ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (8) (1.22 g, 5 mmol), acetic acid (5 g, 83 mmol), NH4OAc (5 g, 65 mmol), and diethyl malonate (2.3 g, 9 mmol). The reaction mixture was refluxed for 48 h. The reaction mixture was cooled to room temperature and washed three times with 50 ml water. The solvent was evaporated in vacuo and the crude product was purified by flash chromatography (ethyl acetate) to yield ethyl 1-(2,2-dicarboethoxyvinyl)-4-oxo-4H-quinolizine-3-carboxylate (12) as a yellow powder (1.58 g, 82%). M.p. 149-151° C. 1H NMR (δ, CDCl3): 1.31 (t, J=7 Hz, 3H), 1.36 (t, J=7 Hz, 3H), 1.42 (t, J=7 Hz, 3H), 4.34 (q, J=7 Hz, 2H), 4.36 (q, J=7 Hz, 2H), 4.41 (q, J=7 Hz, 2H), 7.34 (dd, J=7 Hz, J=7 Hz, 1H), 7.82 (dd, J=8 Hz, 1H), 7.96 (d, J=8 Hz, 1H), 8.05 (s, 1H), 8.60 (s, 1H), 9.50 (d, J=7 Hz). MS: m/z 387.1331; required for C20H21NO7: 387.1318.

Workup

  1. customA 100 ml round-bottom flask equipped with a Dean-Stark trap
  2. temperatureThe reaction mixture was refluxed for 48 h
  3. washwashed three times with 50 ml water
  4. customThe solvent was evaporated in vacuo
  5. customthe crude product was purified by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-5f35593c22a54efaba0bd52cdd1fe460
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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