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

HRID 1442782Notes

Reaction equation

HRID 1442782 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.O.Cl[Sn]Cl.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

6

Reactant 4

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 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 2H. 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 2H
  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-a788980abd0b41e2b1710a41ae3897af
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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