Stannous chloride dihydrate → N2,N2-Diethylpyridine-2,5-diamine

HRID 1030998Notes

Reaction equation

HRID 1030998 reaction equation
[CH2:1]([N:3]([CH2:13][CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][N:5]=1)[CH3:2].O.O.[Sn](Cl)Cl>C(OCC)C.Cl>[NH2:10][C:7]1[CH:8]=[CH:9][C:4]([N:3]([CH2:13][CH3:14])[CH2:1][CH3:2])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 4418042HCID 4418042, compound

Product 1

HCID 11788486N2,N2-Diethylpyridine-2,5-diamineYield 191.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Following procedures similar to those disclosed in Artland, et al., J. Heterocyclic Chem., Vol. 14, 129-134 (1977), the reaction of 10.0 g (0.0512 mole) of 2-diethylamino-5-nitropyridine with 147.0 g (0.659 mole) of tin (II) chloride dihydrate in diethyl ether and concentrated hydrochloric acid produced a residue. This reaction was repeated, and the residues were combined, giving a total of 20 g. The combined residue was purified by column chromatography on silica gel, eluting with acetone to yield 16.2 g of 5-amino-2-diethylaminopyridine as an oil. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customproduced a residue
  2. customgiving a total of 20 g
  3. customThe combined residue was purified by column chromatography on silica gel
  4. washeluting with acetone

Sources & evidence

ORD record
ord-b6c2fd22839f487ca177b75bb9dfb833
Source dataset
uspto-grants-1992_04
Patent number
US05108486

Reaction notes

Loading…