Ammonium Hydroxide → 3-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrile

HRID 517936Notes

Reaction equation

HRID 517936 reaction equation
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[N:12]=[C:11]([C:13]#[N:14])[C:10]([N+:15]([O-])=O)=[C:9]([NH:18][CH3:19])[CH:8]=1.[OH-].[NH4+]>C(O)C>[NH2:15][C:10]1[C:11]([C:13]#[N:14])=[N:12][C:7]([Cl:6])=[CH:8][C:9]=1[NH:18][CH3:19]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 61436Stannous chloride dihydrateHCID 576575586-Chloro-4-methylamino-3-nitro-pyridine-2-carbonitrile

Product 1

HCID 576575713-Amino-6-chloro-4-methylamino-pyridine-2-carbonitrileYield 100.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Tin(II) chloride dihydrate (21 g) was added to a suspension of 6-chloro-4-methylamino-3-nitro-pyridine-2-carbonitrile (6.6 g) in ethanol (150 ml). The mixture was stirred at room temperature for 3 hours. To above red-brown coloured solution was then added ethyl actetate (1000 ml) and followed by 10% aqueous ammonium hydroxide (200 ml). The organic layer were separated, the sticky solid pad was washed with ethyl acetate (5×200 ml). Combined organic layer was then washed with saturated sodium chloride aqueous solution (2×200 ml), dried over sodium sulphate, solvent removed to give a brown solid as expected product (5.7 g). 1H NMR (CD3OD) δ: 6.45 (s, 1H), 2.89 (s, 3H).

Workup

  1. customThe organic layer were separated
  2. washthe sticky solid pad was washed with ethyl acetate (5×200 ml)
  3. washCombined organic layer was then washed with saturated sodium chloride aqueous solution (2×200 ml)
  4. dry with materialdried over sodium sulphate, solvent
  5. customremoved

Sources & evidence

ORD record
ord-ac61fa95a2464656bc00f16d42c9cd84
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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