Hydrochloric Acid → HCID 19754051, compound
Reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N+:11]([O-])=O)=[CH:4][N:3]=1.Cl.[C:15]([OH:21])(=O)[CH2:16][CH2:17][CH2:18][CH3:19].[NH4+].[OH-]>O.[Ni].CO.C1COCC1>[CH2:5]([C:4]1[NH:8][C:7]2[C:2]([N:1]=1)=[N:3][CH:4]=[C:5]([NH:11][C:15](=[O:21])[CH2:16][CH2:17][CH2:18][CH3:19])[CH:6]=2)[CH2:6][CH2:7][CH3:2]Participants
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 2-amino-3,5-dinitropyridine (5.32 g, 28.9 mmol), THF (100 mL), methanol (250 mL) and Raney-nickel (3 mL of a 1:1 suspension in H2O) was stirred under H2 (1 atm.) was stirred for 5 h. The reaction mixture was quickly filtered into a receiving flask containing 5 mL of conc. HCl and the solvent was removed in vacuo at r. t. To this crude 2,3,5-triaminopyridine.HCl was added valeric acid (9.43 mL, 86.7 mmol) and polyphosphoric acid (100 mL) and this mixture was heated to 95° C. for 6 h. The warmed mixture was poured into stirred ice-H2O (200 mL) and this mixture was cooled and neutralized (to pH 4) by the addition of conc. NH4OH. Extraction with EtOAc(3×75 mL), concentration, and purification (SiO2, 5% MeOH/EtOAc) gave the title compound as solid.
Workup
- stirringwas stirred for 5 h
- filtrationThe reaction mixture was quickly filtered into a receiving flask
- additioncontaining 5 mL of conc. HCl
- customthe solvent was removed in vacuo at r
- additionThe warmed mixture was poured
- temperaturethis mixture was cooled
- extractionExtraction
- concentrationwith EtOAc(3×75 mL), concentration, and purification (SiO2, 5% MeOH/EtOAc)
Sources & evidence
- ORD record
- ord-c34944ef6542446595568693eb1e6472
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223499
Reaction notes
Loading…