Sodium Hydroxide → 6-Chloropyridine-2,3-diamine

HRID 1034437Notes

Reaction equation

HRID 1034437 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[N:10]=[C:9]([N+:11]([O-])=O)[C:8]([NH2:14])=[CH:7][CH:6]=1.[OH-].[Na+]>Cl>[Cl:4][C:5]1[N:10]=[C:9]([NH2:11])[C:8]([NH2:14])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 190227926-Chloro-2-nitropyridin-3-amine

Product 1

HCID 106306156-Chloropyridine-2,3-diamineYield 79.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tin (II) chloride (21.8 g) in concentrated hydrochloric acid (30 ml) was added, with cooling, to 6-chloro-3-amino-2-nitropyridine (5 g) and the suspension stirred for 3 hours at room temperature. The pH was adjusted to pH12 (40% NaOH) and the solvent removed in vacuo. The residue was purified by flash column chromatography, eluting with System C (100:8:1), to afford the title compound as a yellow solid (3.29 g).

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was purified by flash column chromatography
  3. washeluting with System C (100:8:1)

Sources & evidence

ORD record
ord-cd53c226bebf4e1c924f09eb8582b479
Source dataset
uspto-grants-1994_05
Patent number
US05317023

Reaction notes

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