Water → 6-Bromo-5-methoxypyridin-2-amine

HRID 2420884Notes

Reaction equation

HRID 2420884 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-])=O)[N:3]=1.O.C([O-])(O)=O.[Na+]>C(O)C>[Br:1][C:2]1[N:3]=[C:4]([NH2:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 126928732-Bromo-3-methoxy-6-nitropyridine

Product 1

HCID 127582096-Bromo-5-methoxypyridin-2-amineYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-3-methoxy-6-nitropyridine (2.0 g, 8.6 mmol) in ethanol (20 mL) was added SnCl2-2H2O (3.9 g, 17 mmol) at room temperature. The reaction was heated at reflux for 2 h. After cooling to room temperature, the reaction mixture was poured into water (50 mL), basified to pH to 8 with saturated NaHCO3 and extracted with ethyl acetate (50×3 mL). The combined organic layers were dried over Na2SO4, evaporated in vacuo and purified by chromatography on silica gel (20% ethyl acetate in petroleum ether) to afford 6-bromo-5-methoxypyridin-2-amine (1.1 g, 65%). 1H-NMR (300 MHz, CDCl3) δ 7.09 (d, J=8.4, 1H), 6.43 (d, J=8.4, 1H), 4.27 (br s, 2H), 3.82 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 2 h
  3. extractionextracted with ethyl acetate (50×3 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. customevaporated in vacuo
  6. custompurified by chromatography on silica gel (20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-2e436691832b4efaab072767a2f7473a
Source dataset
uspto-grants-2011_06
Patent number
US07956052B2

Reaction notes

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