Sodium Methoxide → Ethanone, 1-(4-methoxy-3-pyridinyl)- (9CI)

HRID 1741286Notes

Reaction equation

HRID 1741286 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1Cl)(=[O:3])[CH3:2].[CH3:11][O-:12].[Na+]>O>[C:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:12][CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 14046677HCID 14046677, compound

Product 1

HCID 21835185Ethanone, 1-(4-methoxy-3-pyridinyl)- (9CI)Yield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-acetyl-4-chloropyridine (0.75 g, 4.8 mmol) in sodium methoxide solution (0.5M in methanol, 10.6 ml, 5.3 mmol) was heated at reflux for 1 hour. After cooling water (10 ml) was added and the solvents evaporated. The residue was partitioned between dichloromethane (4×50 ml) and water (50 ml), the combined organic phases dried (MgSO4) and evaporated to afford the title compound (0.58 g, 80%) as a yellow solid. 1H NMR (360 MHz, CDCl3) δ 2.62 (3H, s), 3.98 (3H, s), 6.90 (1H, d, J=5.8 Hz), 8.57 (1H, d, J=5.7 Hz), 8.81 (1H, s).

Workup

  1. temperatureat reflux for 1 hour
  2. additionwas added
  3. customthe solvents evaporated
  4. customThe residue was partitioned between dichloromethane (4×50 ml) and water (50 ml)
  5. dry with materialthe combined organic phases dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-c6598e39e1044c97b102bad2b49362bf
Source dataset
uspto-grants-1999_10
Patent number
US05973156

Reaction notes

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