Dibromomethane → 4-Methyl-[1,3]dioxolo[4,5-c]pyridine

HRID 1647169Notes

Reaction equation

HRID 1647169 reaction equation
[CH3:1][C:2]1[CH:7]([OH:8])[C:6](=[O:9])[CH:5]=[CH:4][N:3]=1.Br[CH2:11]Br.[H-].[Na+]>CS(C)=O.[Cl-].[Na+].O>[CH3:1][C:2]1[C:7]2[O:8][CH2:11][O:9][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 3024DibromomethaneHCID 24758Sodium hydrideHCID 666058152-Methyl-3-hydroxy-4-pyridone

Product 1

HCID 199264514-Methyl-[1,3]dioxolo[4,5-c]pyridine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Methyl-3-hydroxy-4-pyridone (1.25 g, 10 mmol) was dissolved in dry DMSO (20 ml). Dibromomethane (3.5 g, 20 mmol) was added followed by sodium hydride (1 g, >20 mmol, 50-60% in oil). The mixture was left at ambient temperature under stirring for 3 days whereupon it was poured into brine (50 ml). The water-DMSO solution was extracted with methylene chloride (3×50 ml) and the collected extracts were used directly in the next step. A sample for NMR analysis was withdrawn.

Workup

  1. waitThe mixture was left at ambient temperature
  2. extractionThe water-DMSO solution was extracted with methylene chloride (3×50 ml)
  3. customA sample for NMR analysis was withdrawn

Sources & evidence

ORD record
ord-de054ac5c3074316a6b58a239a592cf6
Source dataset
uspto-grants-1995_07
Patent number
US05430042

Reaction notes

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