Tetrahydrofuran → HCID 14229389, compound

HRID 580504Notes

Reaction equation

HRID 580504 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C:4]([NH:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][C:14]=2[C:15]#[N:16])=[CH:3]1.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>CO>[NH2:16][C:15]1[C:14]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:8]=[C:4]2[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[C:3]=12

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 20134102HCID 20134102, compound

Product 1

HCID 14229389HCID 14229389, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture consisting of 3-(1-oxo-2-cyclohexen-3-yl)amino-4-cyanopyridine (3.3 g), potassium carbonate (2.35 g), cuprous chloride (153 mg) and 80 ml of tetrahydrofuran was refluxed for 1 hour. To the mixture was added 25 ml of methanol and the inorganics were removed by filtration. The filtrate liquid was then passed through a packed column and eluted with ethyl acetate to give 3.0 g of solid, mp 237°-242° C. This was recrystallized from n-butyl acetate to give 1.85 g of crystals, mp 242.5°-245° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customthe inorganics were removed by filtration
  3. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-ea6b625500c641fda558bb5b1ac1d7bc
Source dataset
uspto-grants-1988_06
Patent number
US04753950

Reaction notes

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