Potassium Hydroxide → HCID 22168735, compound

HRID 1824563Notes

Reaction equation

HRID 1824563 reaction equation
Br[CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[C:9](=O)[CH3:10].[OH-:12].[K+].O.NN>C(O)CO>[OH:12][CH2:2][CH2:3][N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 22168747HCID 22168747, compound

Product 1

HCID 22168735HCID 22168735, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture containing 1-(2-bromoethyl)-2-acetyl-1H-pyrrole (8.2 g), ethylene glycol (45 mL), 85% potassium hydroxide pellets (8.91 g) and 80% hydrazine hydrate (6.76 mL) was stirred at 200° C. for about 1.5 hr along with simultaneous distillation of volatile materials. The product obtained was extracted with ethyl acetate (2×100 mL). The ethyl acetate layer was washed with water (100 mL), dried over sodium sulfate, filtered and evaporated. The crude product obtained was purified by column chromatography (silica gel 100–200), using ethyl acetate:pet. ether (8:2) as an eluent to obtain 2.2 g of the title compound.

Workup

  1. customThe product obtained
  2. extractionwas extracted with ethyl acetate (2×100 mL)
  3. washThe ethyl acetate layer was washed with water (100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product obtained
  8. customwas purified by column chromatography (silica gel 100–200)

Sources & evidence

ORD record
ord-8dcfcbfe887f4f5f95202359811a07d1
Source dataset
uspto-grants-2006_05
Patent number
US07041837B2

Reaction notes

Loading…