Ammonia → 6-Chloro-5-methyl-3-nitropyridin-2-amine

HRID 505386Notes

Reaction equation

HRID 505386 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[C:4](Cl)[N:3]=1.[NH3:13].C(=O)([O-])[O-].[K+].[K+]>C(O)(C)(C)C>[Cl:1][C:2]1[N:3]=[C:4]([NH2:13])[C:5]([N+:9]([O-:11])=[O:10])=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 122654282,6-Dichloro-3-methyl-5-nitropyridine

Product 1

HCID 218373796-Chloro-5-methyl-3-nitropyridin-2-amineYield 45.1%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,6-dichloro-3-methyl-5-nitropyridine (10.41 g, 50.3 mmol), 28% aqueous ammonia solution (17 ml, 0.25 mol), potassium carbonate (10.4 g, 75.5 mmol) and t-butanol (167 ml) was stirred overnight at 60° C. under nitrogen atmosphere. After stirring at room temperature for 3 hours, a precipitate was filtered and then washed three times with water, thereby yielding the title compound (4.25 g, 22.7 mmol, 45%) as a yellow solid.

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. filtrationa precipitate was filtered
  3. washwashed three times with water

Sources & evidence

ORD record
ord-c22b13e908e1420391a5cb327078e42b
Source dataset
uspto-grants-2010_08
Patent number
US07781452B2

Reaction notes

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