Acetic Acid → Methyl 3-amino-3-(pyridin-3-YL)prop-2-enoate

HRID 1058095Notes

Reaction equation

HRID 1058095 reaction equation
Cl.Cl.[C:3]([CH2:11][C:12]([O:14][CH3:15])=[O:13])(=O)[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][CH:5]=1.C([O-])(=O)C.[Na+].C(O)(=O)C.[NH3:25]>CO.C1(C)C=CC=CC=1>[NH2:25][C:3]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)=[CH:11][C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 517045Sodium AcetateHCID 18673085HCID 18673085, compound

Product 1

HCID 69944552Methyl 3-amino-3-(pyridin-3-YL)prop-2-enoateYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
62.5 °C

Procedure

A suspension of methyl nicotinoylacetate dihydrochloride (50.0 g, 0.23 mol, dried) and sodium acetate (19.0 g, 0.23 mol) in glacial acetic acid (1.4 g, 0.02 mol), toluene (50 g), and methanol (50 g) was heated to 60-65° C. Ammonia (14.0 g, 0.82 mol) was bubbled through the suspension. After four hours, no starting material was present by HPLC. Two-thirds of the solvents were removed by distillation. The solution was stirred at 0° C. for one hour, and the precipitate was collected by filtration and dried to yield 83% of methyl 3-amino-3-(3-pyridyl)-2-propenoate. The crude product was used as is without further purification.

Workup

  1. customTwo-thirds of the solvents were removed by distillation
  2. filtrationthe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-10a4747cbed54d9299b8d740ee1301fa
Source dataset
uspto-grants-2003_02
Patent number
US06515130B1

Reaction notes

Loading…