Stannous chloride dihydrate → 6-Chloro-N2-methylpyridine-2,3-diamine

HRID 515232Notes

Reaction equation

HRID 515232 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.O.O.[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 61436Stannous chloride dihydrateHCID 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 (28-1, 10.5 g, 56 mmol) and tin(II) chloride dihydrate (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 (28-2) as a black solid. HRMS (M+H)+: observed=158.0471, 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-4221ec9e4d984b6c89ea5fabdd9140ce
Source dataset
uspto-grants-2015_08
Patent number
US09108937B2

Reaction notes

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