4-chloro-6-methylfuro[3,2-c]pyridine → HCID 14005231, compound

HRID 1382994Notes

Reaction equation

HRID 1382994 reaction equation
Cl[C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[C:4]([CH3:11])[N:3]=1>C(O)(=O)C.[Zn]>[CH3:11][C:4]1[N:3]=[CH:2][C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 122371844-chloro-6-methylfuro[3,2-c]pyridine

Product 1

HCID 14005231HCID 14005231, compoundYield 91.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 4-chloro-6-methylfuro[3,2-c]pyridine (12.98 g, 0.0776 mol) in glacial acetic acid (160 ml) under a nitrogen atmosphere was added zinc powder (7.0 g, 0.107 mol.). This mixture was heated at 110° C. for 2.5 hours and then filtered hot to remove zinc. The acetic acid solution was evaporated and the residue dissolved in water and made strongly basic by addition of sodium hydroxide. The zinc salts were filtered and washed thoroughly with methylene chloride. The aqueous filtrate was extracted with methylene chloride and the combined washings were dried over anhydrous sodium sulfate, filtered through a charcoal pad and the solvent evaporated to give 9.5 g (87% yield) of pure product, mp: 55°-56° C.

Workup

  1. filtrationfiltered hot
  2. customto remove zinc
  3. customThe acetic acid solution was evaporated
  4. dissolutionthe residue dissolved in water
  5. additionmade strongly basic by addition of sodium hydroxide
  6. filtrationThe zinc salts were filtered
  7. washwashed thoroughly with methylene chloride
  8. extractionThe aqueous filtrate was extracted with methylene chloride
  9. dry with materialthe combined washings were dried over anhydrous sodium sulfate
  10. filtrationfiltered through a charcoal pad
  11. customthe solvent evaporated

Sources & evidence

ORD record
ord-5004f29f6d914e57a7fb592358047ce4
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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