Water → HCID 23320879, compound

HRID 280605Notes

Reaction equation

HRID 280605 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:11]=3[C:10]=2[CH3:19])=O)[CH:2]=1.O.NN.[OH-].[K+].O>C(O)CO>[Br:18][C:15]1[CH:16]=[CH:17][C:11]2[C:10]([CH3:19])=[C:9]([CH2:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[S:13][C:12]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 23320889HCID 23320889, compound

Product 1

HCID 23320879HCID 23320879, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A mixture of 6-bromo-3-methylbenzo[b]thien-2-yl pyrid-3-yl ketone (4.30 g) and hydrazine hydrate (2.60 g) in ethylene glycol (30 ml) was heated under reflux for 2 hours and then cooled. Potassium hydroxide (2.80 g) was added and the temperature was gradually raised to reflux. After heating under reflux for a further 3 hours the solution was cooled and poured into water. The mixture was extracted several times with ethyl acetate and the combined extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was chromatographed on silica gel. Elution with chloroform/petrol (b.p. 40°-60°). (3:1) gave 6-bromo-3-methyl-2-(3-pyridylmethyl)benzo[b]thiophene (3.20 g). A sample crystallised from petrol (b.p. 40°-60°) had m.p. 69°-70°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. temperaturethe temperature was gradually raised
  5. temperatureto reflux
  6. temperatureAfter heating
  7. temperatureunder reflux for a further 3 hours the solution
  8. temperaturewas cooled
  9. extractionThe mixture was extracted several times with ethyl acetate
  10. washthe combined extracts were washed with water
  11. dry with materialdried (Na2SO4)
  12. customEvaporation of the solvent
  13. customgave a solid which
  14. customwas chromatographed on silica gel
  15. washElution with chloroform/petrol (b.p. 40°-60°)

Sources & evidence

ORD record
ord-7f7277b795cd4b3f8f42b93d085146b7
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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