Methanol → 2,6-Dichloro-4-methoxypyridine

HRID 2294774Notes

Reaction equation

HRID 2294774 reaction equation
[CH3:1][OH:2].[H-].[Na+].[Cl:5][C:6]1[CH:11]=[C:10]([N+]([O-])=O)[CH:9]=[C:8]([Cl:15])[N:7]=1>O1CCCC1>[Cl:5][C:6]1[CH:11]=[C:10]([O:2][CH3:1])[CH:9]=[C:8]([Cl:15])[N:7]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 24758Sodium hydrideHCID 38410702,6-Dichloro-4-nitropyridine

Product 1

HCID 33199932,6-Dichloro-4-methoxypyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution containing methanol (0.37 g, 0.0104×1.1 mol), sodium hydride (0.44 g (ca. 60% in mineral oil), 0.0104×1.05 mol) was added, then 2,6-dichloro-4-nitropyridine (2.00. g, 0.0104 mol) was added thereto and the resultant solution was stirred for about 2 hours at room temperature. After it was confirmed that there was no bubbling with the addition of methanol (1.0 g, 0.0355×0.9 mol), the resultant solution was stirred for about another 1 hour. After the reaction solution was partitioned between ethyl acetate and water, the obtained organic layer was washed successively with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride, dried over anhydrous sodium sulfate and thereafter concentrated to obtain the substantially pure end product.

Workup

  1. additionwas added
  2. customAfter the reaction solution was partitioned between ethyl acetate and water
  3. washthe obtained organic layer was washed successively with aqueous saturated sodium hydrogen carbonate and aqueous saturated sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto obtain the substantially pure end product

Sources & evidence

ORD record
ord-63f8636bc1344d00812d615cb3a225a5
Source dataset
uspto-grants-1997_11
Patent number
US05691277

Reaction notes

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