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

HRID 578905Notes

Reaction equation

HRID 578905 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

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 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(4 H)-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, 3 H) 2.86 (br. s, 6 H) 4.06 (q, J=7.1 Hz, 2 H) 6.01-6.11 (m, 2 H) 7.43-7.47 (m, 2 H) 7.48 (s, 1 H).

Sources & evidence

ORD record
ord-7ec7d7c67c3a4b30acac496b4618b80f
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

Loading…