3-Aminopyridine → HCID 14710194, compound

HRID 65697Notes

Reaction equation

HRID 65697 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH:8](OCC)(OCC)[O:9][CH2:10][CH3:11]>Cl>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:1]=[CH:8][O:9][CH2:10][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 100093-AminopyridineHCID 31214Ethyl orthoformate

Product 1

HCID 14710194HCID 14710194, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-aminopyridine (20.0 g, 0.21 m) in excess triethyl orthoformate (100 ml) and ethanolic hydrogen chloride (0.3 ml) was heated under reflux for 72 hours. Ethanol and excess triethyl orthoformate were then removed by distillation over a period of 5 hours. Solid potassium carbonate (100 mg) was added to the residue, and the lasttraces of triethyl orthoformate were removed in vacuo. The residue was then distilled under reduced pressure to yield the desired imido ester, ethyl N-(3-pyridyl)-formimidate, as a colourless liquid, (b.p. 62°/0.5 mm)(24 g, 75%), n.m.r. (CDCl3): δ = 1.4 (t, --CH2CH3), 4.32 (q, --CH2CH3), 7.73 (s, --N=CH--O).

Workup

  1. temperatureunder reflux for 72 hours
  2. customEthanol and excess triethyl orthoformate were then removed by distillation over a period of 5 hours
  3. additionSolid potassium carbonate (100 mg) was added to the residue
  4. customthe lasttraces of triethyl orthoformate were removed in vacuo
  5. distillationThe residue was then distilled under reduced pressure

Sources & evidence

ORD record
ord-35919296686c43bb8d77327ad15ba8b5
Source dataset
uspto-grants-1978_12
Patent number
US04128652

Reaction notes

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