3-Aminopyridine → HCID 14710194, compound

HRID 2052722Notes

Reaction equation

HRID 2052722 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 last traces 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 last traces of triethyl orthoformate were removed in vacuo
  5. distillationThe residue was then distilled under reduced pressure

Sources & evidence

ORD record
ord-a643dca2320c4bff97c637ac478a4b40
Source dataset
uspto-grants-1980_01
Patent number
US04186264

Reaction notes

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