Sodium Hydroxide → 2-Chlorofuro[3,2-b]pyridine

HRID 2116801Notes

Reaction equation

HRID 2116801 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH2:3][C:2]1=O.[OH-].[Na+].P(Cl)(Cl)([Cl:15])=O>>[Cl:15][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 13384344Furo[3,2-B]pyridin-2(3H)-one

Product 1

HCID 107255602-Chlorofuro[3,2-b]pyridine

Procedure

Furopyridone (6, 3.26 g, 24.15 mmol) is treated with phosphorus oxychloride (10 ml) at refluxing temperature for 3 hours. After cooling, the dark solution is poured into ice and basified with aqueous sodium hydroxide to pH ˜9. The mixture is extracted with chloroform. After evaporation of the chloroform, the brown oil is applied to flash column chromatography on silica gel to give chlorofuropyridine as yellow crystalline solid (7).

Workup

  1. temperatureat refluxing temperature for 3 hours
  2. temperatureAfter cooling
  3. extractionThe mixture is extracted with chloroform
  4. customAfter evaporation of the chloroform

Sources & evidence

ORD record
ord-8cfa3d14414644e3abe3b6105661b347
Source dataset
uspto-grants-2008_10
Patent number
US07439374B2

Reaction notes

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