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

HRID 526410Notes

Reaction equation

HRID 526410 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]1[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].C(O[CH:17](OCC)[N:18]([CH3:20])[CH3:19])C>CN(C=O)C>[CH3:17][N:18]([CH3:20])[CH:19]=[C:8]([N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]1=[O:1])[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 9497629Ethyl 2-(2-oxopyridin-1-YL)acetate

Product 1

HCID 131732878ethyl 3-(dimethylamino)-2-(2-oxopyridin-1(2H)-yl)acrylateYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combined ethyl 2-(2-oxopyridin-1(2H)-yl)acetate (500 mg, 2.76 mmol), 1,1-diethoxy-N,N-dimethylmethanamine (2031 mg, 13.80 mmol) and DMF (2 mL) and heated at 100° C. for 15 h. The reaction mixture was diluted with xylenes and concentrated onto Celite® then purified on a 30 g NH silica column (Moritex) eluted with 0 to 100% EtOAc in hexanes to give the title compound (551 mg, 85% yield) as a light yellow solid. MS m/z 237 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.13 (br. s., 3H) 2.77 (br. s., 6H) 3.94-4.08 (m, 2H) 6.17 (td, J=6.7, 1.3 Hz, 1H) 6.36 (dt, J=9.0, 1.1 Hz, 1H) 7.35-7.45 (m, 2H) 7.47 (s, 1H).

Workup

  1. concentrationconcentrated onto Celite®
  2. customthen purified on a 30 g NH silica column (Moritex)
  3. washeluted with 0 to 100% EtOAc in hexanes

Sources & evidence

ORD record
ord-db811c5c6ace4f30804bd6c93ca090fe
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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