Diethyl acetylenedicarboxylate → Ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 326618Notes

Reaction equation

HRID 326618 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])=[CH2:2].[CH2:10]([O:12][C:13]([C:15]#[C:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:14])[CH3:11]>>[CH:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:5]2[C:4]=1[C:17](=[O:18])[CH:16]=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[NH:6]2)=[CH2:2].[CH:1]([C:3]1[CH:4]=[C:5]2[C:7]([C:13](=[O:14])[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:6]2)=[CH:8][CH:9]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 69803Diethyl acetylenedicarboxylateHCID 42600413-Aminostyrene

Product 2

HCID 19735194Ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylateHCID 19735212Ethyl 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate

Procedure

Treatment of 3-ethenylaniline (7 g) with diethylacetylene dicarboxylate (9.4 g), as described in Example 1b, gave ethyl 5-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.16 g), mp 168°-170° C., δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH3), 4.41 (2H, q, CH2), 5.25 and 5.55 (2H, 2dd, =CH2), 6.56 (1H, s, 3H), 7.38 (1H, d, 6-H), 7.62 (1H, t, 7-H), 7.90 (1H, d, 8-H), 8.15 (1H, 2d, CH=) and 11.87 (1H, bs, NH) and ethyl 7-ethenyl-4-oxo-1,4-dihydroquinoline-2-carboxylate (0.46 g), mp 177°-179° C., δ (360 MHz, DMSO-d6) 1.37 (3H, t, CH3),4.42 (2H, q, CH2), 5.47 and 5.99 (2H, 2d, =CH2), 6.65 (1H, bs, 3-H), 6.84 (1H, 2d, CH=), 7.54 (1H, d, 6-H) and 7.93 (1H, s, 8-H), 8.04 (1H, d, 5-H), 11.97 (1H, bs, NH).

Sources & evidence

ORD record
ord-a42888f17b13479582e4cf1472bdd5ba
Source dataset
uspto-grants-1993_12
Patent number
US05270309

Reaction notes

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