Potassium Hydroxide → HCID 178441054, compound

HRID 1067704Notes

Reaction equation

HRID 1067704 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([CH:18]3[CH2:20][CH2:19]3)=O)=[CH:12][CH:11]=2)[N:3]=[CH:2]1.O.NN.[OH-].[K+]>C(O)COCCOCCO>[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:18][CH2:19][CH3:20])=[CH:14][CH:15]=2)[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 178519714HCID 178519714, compound

Product 1

HCID 178441054HCID 178441054, compound

Reagents, catalysts & solvents 1

HCID 8172Triethylene GlycolSolvent

Procedure

0.8 mmol of cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl ketone (Example 61), 4 mmol of hydrazine hydrate and 3.2 mmol of KOH in 30 ml of triethylene glycol are brought to reflux for 2 hours. The solvent is evaporated off under reduced pressure, and the crude product is extracted with dichloromethane and purified by rotatory chromatography (eluent:dichloromethane/methanol (99:1)-(90:10), ammoniacal atmosphere). The product is crystallized in the form of hydrogen maleate from diethyl ether and ethanol.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe solvent is evaporated off under reduced pressure
  3. extractionthe crude product is extracted with dichloromethane
  4. custompurified by rotatory chromatography (eluent:dichloromethane/methanol (99:1)-(90:10), ammoniacal atmosphere)
  5. customThe product is crystallized in the form of hydrogen maleate from diethyl ether and ethanol

Sources & evidence

ORD record
ord-10382802520a4618b69fdd296f9992d0
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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