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Triethylene Glycol → 2-(3-Pyridylmethyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35193
Notes
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Reaction equation

HRID 35193 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:23][CH2:22][CH2:21][O:20]4)[CH:15]=3)[CH:10]=2)=O)[CH:2]=1.C(O)COCCOCCO.NN.[OH-].[K+]>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:19]4([CH3:24])[O:20][CH2:21][CH2:22][O:23]4)[CH:15]=3)[CH:10]=2)[CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 156122422-(3-Pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

Product 1

HCID 156122432-(3-Pyridylmethyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthaleneYield 62%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
160 °C

Procedure

A mixture of 270 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, 7 ml of triethylene glycol, 1 ml of anhydrous hydrazine and 500 mg of potassium hydroxide were heated at 160° C. for 30 minutes. The temperature was then raised to 210° C. for 1 hour. The mixture was cooled, poured into water and extracted with methylene chloride. The organic layer was dried over sodium sulfate, the solvent removed under reduced pressure and the residue chromatographed on silica gel to give 160 mg of 2-(3-pyridylmethyl)-6-(2-methyl-1,3dioxolan-2-yl)naphthalene as an oil.

Workup

  1. temperatureThe temperature was then raised to 210° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-9b438c38abb14a318e2a01f24f8f5b42
Source dataset
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04766127

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes