Ethyl 8-(4-Methoxyphenyl)-4-Oxo-4H-Quinolizine-3-Carboxylate → Ethyl 8-(Naphth-1-yl)-4-Oxo-4H-Quinolizine-3-Carboxylate

HRID 48915Notes

Reaction equation

HRID 48915 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][N:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]3=[O:24])=[CH:5][CH:4]=1>C(OCC)(=O)C>[C:6]1([C:9]2[CH:10]=[CH:11][N:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[C:14]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]3=[O:24])[C:7]2[C:8](=[CH:8][CH:3]=[CH:4][CH:5]=2)[CH:3]=[CH:4][CH:5]=1

Participants

3

Reactant 1

HCID 20634155Ethyl 8-(4-Methoxyphenyl)-4-Oxo-4H-Quinolizine-3-Carboxylate

Product 1

HCID 20634160Ethyl 8-(Naphth-1-yl)-4-Oxo-4H-Quinolizine-3-CarboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using the procedure as described in Example 17 (i.e., for compound 22) ethyl 8-(napthy-1-yl)-4-oxo-4H-quinolizine-3-carboxylate (23) was isolated in 51% yield by flash chromatography (ethyl acetate). M.p. 245-247° C. 1H NMR (δ, CDCl3): 1.48 (t, J=7 Hz, 3H), 4.48 (q, J=7 Hz, 2H), 6.73 (d, J=8 Hz, 1H), 7.40 (dd, J=2 Hz, J=8 Hz, 1H), 7.55-7.64 (m, 4H), 7.72 (s, 1H), 7.91 (d, J=8 Hz, 1H), 7.98-8.06 (m, 2H), 8.48 (d, J=8 Hz, 1H), 9.52 (d, J=8 Hz, 1H). MS: m/z 343.1213; required for C22H17NO3: 343.1208.

Sources & evidence

ORD record
ord-518e2a85d2d24828a7fd7a4f0226eb1f
Source dataset
uspto-grants-2004_03
Patent number
US06706528B2

Reaction notes

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