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

HRID 1393038Notes

Reaction equation

HRID 1393038 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 10 (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 on aqueous NaOH 1M and extracted with ethyl acetate. After drying over Na2SO4, the solvent was then evaporated and 11 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
  4. custom11 was isolated as a colorless solid (370 mg, 2.6 mmol, HPLC Rt 1.3 min, FIA ES+ 143.0)

Sources & evidence

ORD record
ord-e36af1263d424eb897e5e607beff04d6
Source dataset
uspto-grants-2008_03
Patent number
US07345054B2

Reaction notes

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