Methacrylonitrile → HCID 20228177, compound

HRID 1731669Notes

Reaction equation

HRID 1731669 reaction equation
[Na].[NH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[NH2:3].[C:10](#[N:14])[C:11]([CH3:13])=[CH2:12]>C(O)C>[NH2:14][C:10]1[CH:11]([CH3:13])[CH2:12][N:2]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=2)[N:3]=1

Participants

5

Reactant 3

HCID 31368MethacrylonitrileHCID 786452-HydrazinopyridineHCID 5360545Sodium

Product 1

HCID 20228177HCID 20228177, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.02 g. amount of sodium metal is dissolved in 250 ml. of absolute ethanol, then 21.8 g. of 2-hydrazinopyridine is added, followed by 13.4 g. of methacrylonitrile. The reaction mixture is refluxed for 16 hours, then the solvent is removed in vacuo. The solid is recrystallized twice from 3A ethanol after treatment with activated charcoal to give 4.30 g. of a tan solid. The above recrystallization filtrates are combined and evaporated in vacuo to a solid. The solid is dissolved in dichloromethane and passed through a hydrous magnesium silicate. The filtrate is concentrated while adding hexane at reflux to crystallize an additional 16.4 g. of the desired product (total 20.79 g.) as tan crystals, m.p. 149°-151° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 16 hours
  2. customthe solvent is removed in vacuo
  3. customThe solid is recrystallized twice from 3A ethanol after treatment with activated charcoal
  4. customto give 4.30 g
  5. customThe above recrystallization filtrates
  6. customevaporated in vacuo to a solid
  7. dissolutionThe solid is dissolved in dichloromethane
  8. concentrationThe filtrate is concentrated
  9. additionwhile adding hexane
  10. temperatureat reflux
  11. customto crystallize an additional 16.4 g

Sources & evidence

ORD record
ord-c20c62e68d8948c196e8c3e40ab2ff39
Source dataset
uspto-grants-1986_11
Patent number
US04622401

Reaction notes

Loading…