Dimethylformamide diethylacetal → Ethyl 2-(6-chloropyridin-3-yl)-3-(dimethylamino)acrylate

HRID 37883

Reaction equation

HRID 37883 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C: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>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8](=[CH:17][N:18]([CH3:20])[CH3:19])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 70913Dimethylformamide diethylacetalHCID 15661146Ethyl 2-(6-chloropyridin-3-yl)acetate

Product 1

HCID 72537728Ethyl 2-(6-chloropyridin-3-yl)-3-(dimethylamino)acrylate

Conditions

Temperature
90 °C

Procedure

3.99 g (20.0 mmol) of the compound from Example 1A are dissolved in 13.7 ml of dimethylformamide diethyl acetal, and the mixture is stirred with microwave irradiation at 90° C. for 30 min. The mixture is then concentrated on a rotary evaporator, and the residue is chromatographed on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol 20:1).

Workup

  1. concentrationThe mixture is then concentrated on a rotary evaporator
  2. customthe residue is chromatographed on silica gel 60 (mobile phase: dichloromethane→dichloromethane/methanol 20:1)

Sources & evidence

ORD record
ord-16cc391b4b8f4a33be01b15eb6e4129f
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Linked notes

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