Methylamine → HCID 54506621, compound

HRID 66120Notes

Reaction equation

HRID 66120 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.[CH3:19][NH2:20]>CO>[CH3:19][NH:20][CH2:2][CH2:3][O:4][C:5]1[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=1[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 53663043HCID 53663043, compound

Product 1

HCID 54506621HCID 54506621, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

16 gm of 2-[o-(β-chloro-ethoxy)-styryl]-pyridine (m.p. 57°-59° C.) were dissolved in 50 ml of methanol, the solution was mixed at -15° C. with 120 ml of liquid methylamine freshly removed from a bomb, and the mixture was heated at 80° C. in an autoclave for 4 hours. After cooling and releasing the pressure, the contents of the autoclave were evaporated, the residue was dissolved in dilute acetic acid, and the solution was extracted twice with ether to remove weakly basic products. Then, the aqueous phase was made alkaline with 2 N sodium hydroxide solution and was extracted with ethyl acetate. After drying the ethyl acetate extract with sodium sulfate and distilling off the solvent, an oily residue was obtained which crystallized after standing overnight. 13.6 gm (88.2% of theory) of 2-[o-(β-methylaminoethoxy)-styryl]-pyridine were obtained.

Workup

  1. customfreshly removed from a bomb
  2. temperatureAfter cooling
  3. customthe contents of the autoclave were evaporated
  4. dissolutionthe residue was dissolved in dilute acetic acid
  5. extractionthe solution was extracted twice with ether
  6. customto remove weakly basic products
  7. extractionwas extracted with ethyl acetate
  8. dry with materialAfter drying the ethyl acetate
  9. extractionextract with sodium sulfate
  10. distillationdistilling off the solvent
  11. customan oily residue was obtained which
  12. customcrystallized

Sources & evidence

ORD record
ord-3a3ea4e12753436b83448b425a4dbada
Source dataset
uspto-grants-1978_12
Patent number
US04130650

Reaction notes

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