Stannous Chloride → 6-Chloro-N2-methylpyridine-2,3-diamine

HRID 629856Notes

Reaction equation

HRID 629856 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([N+:10]([O-])=O)=[CH:4][CH:3]=1.[Sn](Cl)Cl.[OH-].[Na+].C(OCC)(=O)C>Cl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([NH2:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 107500946-chloro-N-methyl-3-nitropyridin-2-amineHCID 23721230NaOH EtOAc

Product 1

HCID 249039426-Chloro-N2-methylpyridine-2,3-diamine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

6-Chloro-N-methyl-3-nitropyridin-2-amine (1-1, 10.5 g, 56 mmol) and tin(II) chloride dehydrate (50.5 g, 224 mmol) were suspended in concentrated HCl (80 mL) and refluxed overnight. The solution was cooled to room temperature and then added very slowly to a NaOH/ethyl acetate solution at −78° C., until the solution had a slightly basic pH. The suspension was washed with sodium bicarbonate, brine, dried over sodium sulfate, filtered, and concentrated to produce 6-chloro-N2-methylpyridine-2,3-diamine (1-2) as a black solid. HRMS (M+H)+: observed=158.0487, calculated=158.0480.

Workup

  1. temperaturerefluxed overnight
  2. washThe suspension was washed with sodium bicarbonate, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-64187e08ff7349419fd6ae960a38d822
Source dataset
uspto-grants-2016_04
Patent number
US09315518B2

Reaction notes

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