Ethylene Glycol → HCID 68193208, compound

HRID 1626808Notes

Reaction equation

HRID 1626808 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[N:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=2)=O)=[CH:4][CH:3]=1.O.NN.[OH-].[K+].O.C(O)[CH2:25][OH:26]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:25][OH:26])=[N:12][CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 68193231HCID 68193231, compound

Product 1

HCID 68193208HCID 68193208, compoundYield 41%

Conditions

Temperature
140 °C

Procedure

(4-Bromophenyl)(6-methoxypyridin-3-yl)methanone (0.88 g, 3.0 mmol), hydrazine monohydrate (1.5 mL, 30 mmol) and potassium hydroxide (0.60 g, 12 mmol) were dissolved in ethylene glycol (10 mL), followed by stirring at 140° C. for 20 minutes. After the reaction solution was cooled to room temperature, water was added, followed by extraction with diethyl ether. After the organic layer was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.38 g, 1.2 mmol) as a colorless oil (yield 41%).

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with diethyl ether
  3. concentrationAfter the organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.30 (hexane/ethyl acetate=1/1) by thin layer chromatography was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c03220af5870442ba6b252367b6beed9
Source dataset
uspto-grants-2014_07
Patent number
US08785462B2

Reaction notes

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