Dimethylformamide dimethyl acetal → Ethyl 2-[2-(dimethylamino)vinyl]-5-nitronicotinate

HRID 365072Notes

Reaction equation

HRID 365072 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:16][N:17]([CH:19](OC)OC)[CH3:18]>>[CH3:16][N:17]([CH3:19])[CH:18]=[CH:1][C:2]1[N:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 287239Ethyl 2-methyl-5-nitronicotinate

Product 1

HCID 54323216Ethyl 2-[2-(dimethylamino)vinyl]-5-nitronicotinate

Procedure

A solution containing 20.88 g of ethyl 2-methyl-5-nitronicotinate in 100 mL 1,1-dimethoxytrimethylamine is heated at reflux for three hours and 15 minutes. The mixture is cooled and the solid collected by filtration, washed with methanol and air dried to give 26 g of the desired enamine as a dark red solid mp 176°-179° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for three hours and 15 minutes
  3. temperatureThe mixture is cooled
  4. filtrationthe solid collected by filtration
  5. washwashed with methanol and air
  6. customdried

Sources & evidence

ORD record
ord-185a262ea8de4263be3a87366580942d
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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