Dimethylformamide diethylacetal → 3-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

HRID 1526080Notes

Reaction equation

HRID 1526080 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].C(O[CH:16](OCC)[N:17]([CH3:19])[CH3:18])C>>[CH2:1]([O:3][C:4](=[O:12])[C:5]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)=[CH:16][N:17]([CH3:19])[CH3:18])[CH3:2]

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 96490Ethyl 3-pyridylacetate

Product 1

HCID 687048643-(Dimethylamino)-2-pyridin-3-yl-acrylic acid ethyl ester

Procedure

37.4 g (226 mmol) pyridin-3-ylacetic acid ethyl ester are heated in 100 g (679 mmol) dimethylformamide diethyl acetal overnight at 100° C. After cooling, the mixture is concentrated and the residue is pre-purified by means of flash chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1→ethyl acetate/ethanol 9:1). The product obtained is subjected to fine purification by vacuum distillation (1 mbar, 200° C. bath temperature).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture is concentrated
  3. customthe residue is pre-purified by means of flash chromatography on silica gel (mobile phase: gradient cyclohexane/ethyl acetate 1:1→ethyl acetate/ethanol 9:1)
  4. customThe product obtained
  5. distillationis subjected to fine purification by vacuum distillation (1 mbar, 200° C. bath temperature)

Sources & evidence

ORD record
ord-51e86c00346f48599f06eaa5efbfaf91
Source dataset
uspto-grants-2015_07
Patent number
US09085572B2

Reaction notes

Loading…