Sodium Hydroxide → 2-Chloro-5-methylpyridin-4-amine

HRID 2374135Notes

Reaction equation

HRID 2374135 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([CH3:11])=[CH:4][N+:3]=1[O-].[OH-].[Na+]>C(O)(=O)C.[Fe]>[NH2:8][C:6]1[C:5]([CH3:11])=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 123180102-Chloro-5-methyl-4-nitropyridine N-oxide

Product 1

HCID 126437062-Chloro-5-methylpyridin-4-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron (1.0 g) was added to a solution of 2-chloro-5-methyl-4-nitropyridine N-oxide (500 mg, 2.6 mmol) in glacial acetic acid (10 mL). The reaction mixture was then heated at 100° C. for 20 minutes. The suspension was poured onto aqueous NaOH (1M) and extracted with ethyl acetate. After drying over Na2SO4, the solvent was then evaporated and the title compound was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialAfter drying over Na2SO4
  3. customthe solvent was then evaporated

Sources & evidence

ORD record
ord-c5e2cccd25ce4af194b103f0735c97d3
Source dataset
uspto-grants-2008_12
Patent number
US07462612B2

Reaction notes

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