Sodium Hydroxide → 4-chloro-6-methylfuro[3,2-c]pyridine

HRID 1382993Notes

Reaction equation

HRID 1382993 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=O)[C:5]2[CH:9]=[CH:10][O:11][C:4]=2[CH:3]=1.P(Cl)(Cl)([Cl:14])=O.[OH-].[Na+]>>[Cl:14][C:6]1[C:5]2[CH:9]=[CH:10][O:11][C:4]=2[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 12237176HCID 12237176, compound

Product 1

HCID 122371844-chloro-6-methylfuro[3,2-c]pyridineYield 96%

Conditions

Temperature
100 °C

Procedure

A mixture of 6-methylfuro[3,2-c]pyridin-4(5H)-one (11.9 g, 0.08 mol) and phosphorus oxychloride (15.2 ml, 0.163 mol) was heated, under a nitrogen atmosphere, at 100° C. for 1.5 hours. The cooled blackish liquid was poured onto crushed ice and the solution made basic with sodium hydroxide solution. The precipitated product was extracted into methylene chloride. This solution was dried over anhydrous sodium sulfate, filtered through a pad of charcoal and evaporated. Pure product was collected by filtration after the residue was triturated with hexane to give 12.9 g (96% yield), mp: 64.5°-66° C.

Workup

  1. additionThe cooled blackish liquid was poured
  2. customonto crushed ice
  3. extractionThe precipitated product was extracted into methylene chloride
  4. dry with materialThis solution was dried over anhydrous sodium sulfate
  5. filtrationfiltered through a pad of charcoal
  6. customevaporated
  7. filtrationPure product was collected by filtration after the residue
  8. customwas triturated with hexane
  9. customto give 12.9 g (96% yield), mp: 64.5°-66° C.

Sources & evidence

ORD record
ord-170d0d1eee784ba2989566044e8bbf28
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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