Nitric Acid → 5-Chloro-4-methyl-3-nitropyridin-2-amine

HRID 633583

Reaction equation

HRID 633583 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[NH4+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 3181862-Amino-5-chloro-4-methylpyridine

Product 1

HCID 214641365-Chloro-4-methyl-3-nitropyridin-2-amineYield 58.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-10 °C

Procedure

5-chloro-4-methylpyridin-2-amine (30 g, 210 mmol) was dissolved in concentrated sulfuric acid (150 mL), and the solution was cooled to −10° C. Nitric acid (36 mL, 806 mmol) was added dropwise. The reaction mixture was stirred at 55° C. for 3 hours. The reaction mixture was poured into an ice/water mixture, and the pH was adjusted to 8 by addition of concentrated aqueous ammonium hydroxide (22%). The resulting suspension was filtered, and the solids were washed with water and dried under vacuum to provide the title compound (23 g, 123 mmol, 58.3% yield).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe solids were washed with water
  3. customdried under vacuum

Sources & evidence

ORD record
ord-a2100a516536452dab4483736fdd0f16
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Linked notes

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