Ethanol → HCID 178513340, compound

HRID 1927244Notes

Reaction equation

HRID 1927244 reaction equation
C(O)C.[NH2:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].Cl.[NH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>O>[NH2:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]([NH:14][OH:15])=[NH:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 178513340HCID 178513340, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethanol (10 mL) and 2-amino-nicotinonitrile (590 mg) were added hydroxylamine hydrochloride (510 mg) and potassium carbonate (1.4 g) at room temperature, which was stirred for 7 hours and 30 minutes under reflux. After this, the reaction mixture was stirred for 13 hours and 30 minutes at room temperature, then water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, after which the filtrate was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the titled compound (520 mg) as a cis-trans mixture. The titled compound was used in the subsequent reaction without further purification.

Workup

  1. temperatureunder reflux
  2. stirringAfter this, the reaction mixture was stirred for 13 hours and 30 minutes at room temperature
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customafter which the filtrate was evaporated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-6af7e5e05e4449da83c9a0dae721c8c4
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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