6-Bromo-3-methoxy-2-nitropyridine → 2-Amino-6-bromo-3-methoxypyridine

HRID 1772884Notes

Reaction equation

HRID 1772884 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1>[Fe].CC(O)=O>[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 226151626-Bromo-3-methoxy-2-nitropyridine

Product 1

HCID 575629062-Amino-6-bromo-3-methoxypyridineYield 81.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-bromo-3-methoxy-2-nitropyridine (14.4 g, 61.8 mmol), AcOH (200 mL) and Fe powder (14.0 g, 0.25 mol) was stirred at 90° C. for 1.5 h. After cooling to rt and dilution with EtOAc the mixture was filtered through celite and the filtrate concentrated in vacuo. Purification by flash chromatography eluting with DCM yielded the title compound (10.2 g, 50.2 mmol) as a white solid.

Workup

  1. temperatureAfter cooling to rt
  2. filtrationdilution with EtOAc the mixture was filtered through celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by flash chromatography
  5. washeluting with DCM

Sources & evidence

ORD record
ord-796c49612d6244109b8cd94804124d62
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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