Stannous chloride dihydrate → 3-Methoxy-4-pyridin-2-ylaniline

HRID 734257Notes

Reaction equation

HRID 734257 reaction equation
O.O.[Sn](Cl)Cl.[CH3:6][O:7][C:8]1[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1>CO>[CH3:6][O:7][C:8]1[CH:13]=[C:12]([CH:11]=[CH:10][C:9]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[NH2:14]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 219565262-(2-Methoxy-4-nitrophenyl)pyridine

Product 1

HCID 219565203-Methoxy-4-pyridin-2-ylaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tin(II) chloride dihydrate (6.77 g, 30.0 mmol) and 2-(2-methoxy-4-nitrophenyl)pyridine (2.30 g, 10.0 mmol) were combined in MeOH (100 mL) and stirred at reflux for 18 h. The reaction mixture was then cooled to RT and concentrated in vacuo. The residue was then partitioned with EtOAc (200 mL) and 1N aqueous NaOH (100 mL). The aqueous layer was washed with EtOAc (3×75 mL), and the combined EtOAc layers were back-extracted with H2O (100 mL), dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was purified by SiO2 chromatography, eluting with 2:1 EtOAc:hexanes to afford 3-methoxy4-pyridin-2-ylaniline as an amber oil. 1H-NMR (CDCl3, 300 MHz) δ 8.63 (m, 1H), 7.78 (d, 1H), 7.57-7.67 (m, 2H), 7.04-7.13 (m, 1H), 6.34-6.41(dd, 1H), 6.26 (d, 1H), 3.72-3.92 (s, 2H), 3.72 (s, 3H).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was then partitioned with EtOAc (200 mL) and 1N aqueous NaOH (100 mL)
  4. washThe aqueous layer was washed with EtOAc (3×75 mL)
  5. extractionthe combined EtOAc layers were back-extracted with H2O (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was purified by SiO2 chromatography
  10. washeluting with 2:1 EtOAc

Sources & evidence

ORD record
ord-22a558d78f68463fb9cf25743f3522a6
Source dataset
uspto-grants-2009_09
Patent number
US07592337B2

Reaction notes

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