Methoxyacetone → 3-Methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1756100Notes

Reaction equation

HRID 1756100 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)N.[CH3:9][O:10][CH2:11][C:12](=O)[CH3:13]>C(O)C>[CH3:9][O:10][C:11]1[C:8]2[C:3](=[N:4][CH:5]=[CH:6][CH:7]=2)[NH:1][C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 22172MethoxyacetoneHCID 786452-Hydrazinopyridine

Product 1

HCID 199168183-Methoxy-2-methyl-1H-pyrrolo[2,3-b]pyridineYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7,4 g (68 mmol) 2-hydrazinopyridine and 6,0 g (68 mmol) methoxyaceton in 50 ml of ethanol was refluxed for 1 h. The solvent was removed under reduced pressure. The resulting oil was dissolved in diethylene glycol and refluxed for 1,5 h. The mixture was allowed to cool and was poured into ice-water. Extraction with methylene chloride gave an black oily residue which was treated with boiling petroleumether (60-80). After decanting the solvent was allowed to cool and the precipitated product filtered of affording 4,5 g (41%) pure title compound as a yellow solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe resulting oil was dissolved in diethylene glycol
  3. temperaturerefluxed for 1,5 h
  4. temperatureto cool
  5. additionwas poured into ice-water
  6. extractionExtraction with methylene chloride
  7. customgave an black oily residue which
  8. additionwas treated
  9. customAfter decanting the solvent
  10. temperatureto cool
  11. filtrationthe precipitated product filtered

Sources & evidence

ORD record
ord-fdfb30b531b3427497b8373a7e1d2497
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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