2-Amino-4-chloropyridine → 2-Amino-4-Methoxypyridine

HRID 2402373Notes

Reaction equation

HRID 2402373 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH3:9][O-:10].[Na+]>CS(C)=O>[CH3:9][O:10][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1

Participants

4

Reactant 2

HCID 5818662-Amino-4-chloropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 108987152-Amino-4-MethoxypyridineYield 16%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 4-chloropyridin-2-amine (3 g, 23.2 mmol) in DMSO (60 mL) was added sodium methoxide (12.6 g, 232 mmol) and the mixture was then stirred at 150° C. for 3 hours then poured into ice-water. The product was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water (50 mL) and brine (50 mL), dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography using a solvent system of 50% petroleum ether/EtOAc to give 4-methoxypyridin-2-amine (460 mg, 16%) as a yellow solid MS ESI calcd for C6H8N2O [M+H]+ 125, found 125.

Workup

  1. extractionThe product was extracted with EtOAc (2×100 mL)
  2. washthe combined organic layers were washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-880eaf4a150e48128a275ce97b3fb75e
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Reaction notes

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