Picolinic acid → HCID 6612277, compound

HRID 257519Notes

Reaction equation

HRID 257519 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](O)=O.[NH4+].[OH-]>>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[CH:5][CH:6]=2

Participants

4

Reactant 3

HCID 1018Picolinic acidHCID 99562,3-DiaminopyridineHCID 14923Ammonium Hydroxide

Product 1

HCID 6612277HCID 6612277, compoundYield 56.1%

Procedure

A solution of 2,3-diaminopyridine (1.1 g, 10 mmol) and 2-picolinic acid (1.23 g, 10 mmol) in polyphosphoric acid (10 ml) was heated to 160° C. for 4 hours. The hot solution was poured into ice water and the pH adjusted to pH 9 with conc. NH4OH. The resulting precipitate was filtered and air dried. This crude product was recrystallized from EtOH to give 1.1 g (56%) of the title compound, m.p. 139°-142° C. Anal. Calcd for C11H8N4 : C, 67.34; H, 4.11; N, 28.36. Found: C, 66.88; H, 4.17; N, 8.36.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customair dried
  3. customThis crude product was recrystallized from EtOH

Sources & evidence

ORD record
ord-b4a2008650224066bc1bfea2ea401851
Source dataset
uspto-grants-1993_11
Patent number
US05262426

Reaction notes

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