Dimethylformamide diethylacetal → ethyl 3-(dimethylamino)-2-(4-oxopyridin-1(4H)-yl)acrylate

HRID 526405Notes

Reaction equation

[O:1]=[C:2]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3]1.C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>>[CH3:17][N:18]([CH3:20])[CH:19]=[C:8]([N:5]1[CH:4]=[CH:3][C:2](=[O:1])[CH:7]=[CH:6]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

Reactant 2

HCID 70913Dimethylformamide diethylacetal

HCID 12254000ethyl 2-(4-oxopyridin-1(4H)-yl)acetate

Product 1

HCID 131732877ethyl 3-(dimethylamino)-2-(4-oxopyridin-1(4H)-yl)acrylate

Procedure

The title compound was prepared in a manner similar to Example Preparation 10 using ethyl 2-(4-oxopyridin-1(4H)-yl)acetate and 1,1-diethoxy-N,N-dimethylmethanamine to give the title compound. MS m/z 237 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.16 (t, J=7.1 Hz, 3H) 2.86 (br. s, 6H) 4.06 (q, J=7.1 Hz, 2H) 6.01-6.11 (m, 2H) 7.43-7.47 (m, 2H) 7.48 (s, 1H).

Sources & evidence

ORD record: ord-f192d52ac33a455ebb7eae41601a4fa2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09345713B2

Reaction notes

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