Dimethyl acetylenedicarboxylate → Dimethyl 5-chloro-1-(4-methoxybenzyl)-6-oxo-1,6-dihydropyridine-3,4-dicarboxylate

HRID 1752592Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:18])[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[CH:5]=C(Cl)N=1.[CH3:19][O:20][C:21](=[O:28])[C:22]#[C:23][C:24]([O:26][CH3:27])=[O:25]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[C:3](=[O:18])[N:4]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)[CH:5]=[C:22]([C:21]([O:20][CH3:19])=[O:28])[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

Conditions

Temperature: 150 °C

Procedure

Compound (8) (2.0 g, 7.01 mmol) and 2-butynedioic acid dimethyl ester (2.99 g, 21.04 mmol) were added to xylene (40 ml). The reaction was heated at about 150° C. for about 16 h. The reaction was cooled to about 25° C. The reaction mixture was filtered through a Büchner funnel to afford the title compound (0.9 g, 2.338 mmol, 33.3% yield). LC-MS (ESI+): m/e 366 (M+H)+, Rt: 1.98 min; 1H-NMR (DMSO-d6, 400 MHz): δ=3.73 (s, 3H), 3.79 (s, 3H), 3.88 (s, 3H), 5.21 (s, 2H), 6.91 (d, 2H, J=6.8 Hz), 7.34 (d, 2H, J=6.8 Hz), 8.81 (s, 1H).

Workup

temperatureThe reaction was cooled to about 25° C
filtrationThe reaction mixture was filtered through a Büchner funnel

Sources & evidence

ORD record: ord-167560c6cb954c9ca7c5b69d0a89d845
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163019B2

Reaction notes

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