2-Aminopyridine → HCID 13633211, compound

HRID 2118495Notes

Reaction equation

HRID 2118495 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[N+:13]1([O-:22])[C:14]([C:19]([OH:21])=O)=[CH:15][CH:16]=[CH:17][CH:18]=1.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1>CN(C)C=O>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[NH:23][C:19]([C:14]1[N+:13]([O-:22])=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:21]

Participants

5

Reactant 3

HCID 104392-AminopyridineHCID 682631,1'-CarbonyldiimidazoleHCID 69986Pyridine-2-carboxylic acid 1-oxide

Product 1

HCID 13633211HCID 13633211, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,1'-Carbonyldiimidazole (4.254 g, 26.2 mol) was added to a solution of picolinic acid N-oxide (3.318g, 23.9 mol) in dry dimethylformamide (50 ml). After 4 hours, 2-aminopyridine (2.466 g, 26.2 mol) was added. After 1 hour, the solution was warmed to 100° for 80 minutes and cooled to room temperature. After 18 hours the solution was subjected to evaporation in vacuo to give an oil which slowly crystallised. The solid was recrystallised from EtOH to give the title compound (3.775 g) as needles, m.p. 140°-5°.

Workup

  1. waitAfter 1 hour
  2. temperaturethe solution was warmed to 100° for 80 minutes
  3. customAfter 18 hours the solution was subjected to evaporation in vacuo
  4. customto give an oil which
  5. customslowly crystallised
  6. customThe solid was recrystallised from EtOH

Sources & evidence

ORD record
ord-3fe7cfe342a242d3a439e166c0fd66f1
Source dataset
uspto-grants-1987_07
Patent number
US04678794

Reaction notes

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