Potassium Hydroxide → HCID 23320895, compound

HRID 280608Notes

Reaction equation

HRID 280608 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[CH3:14])=O)[CH:2]=1.O.NN.[OH-].[K+]>C(O)CO>[Br:19][C:16]1[CH:17]=[CH:18][C:11]2[O:10][C:9]([CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[C:13]([CH3:14])[C:12]=2[CH:15]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 29076030HCID 29076030, compound

Product 1

HCID 23320895HCID 23320895, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-bromo-3-methylbenzofuran-2-yl pyrid-3-yl ketone free base (2.67 g) and hydrazine hydrate (1.80 g) in ethylene glycol (30 ml) was heated at 120° C. for 2.5 hours. The mixture was cooled, potassium hydroxide (1.80 g) was added and the temperature was raised to 120° again and maintained at this temperature for 1 hour. Dilution with water and ether extraction gave an oil which was chromatographed on silica gel. Elution with chloroform gave a solid which was crystallised from petrol (b.p. 80°-100°) to give 5-bromo-3-methyl-2-(3-pyridylmethyl)benzofuran (2.00 g), m.p. 57°-58°.

Workup

  1. temperatureThe mixture was cooled
  2. temperaturethe temperature was raised to 120° again
  3. temperaturemaintained at this temperature for 1 hour
  4. extractionDilution with water and ether extraction
  5. customgave an oil which
  6. customwas chromatographed on silica gel
  7. washElution with chloroform
  8. customgave a solid which
  9. customwas crystallised from petrol (b.p. 80°-100°)

Sources & evidence

ORD record
ord-562c8fdf315b49fcab10840033e06d3a
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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