Ethanol → HCID 178456338, compound

HRID 80899Notes

Reaction equation

HRID 80899 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C(O)C.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>O>[OH:23][NH:22][C:14](=[NH:15])[C:13]1[CH:16]=[CH:17][C:10]([N:7]2[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]2)=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 434217446-(4-Isopropylpiperazin-1-yl)nicotinonitrile

Product 1

HCID 178456338HCID 178456338, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-(4-isopropylpiperazin-1-yl)nicotinonitrile (2.3 g, 10 mmol), ethanol (25 mL), hydroxylamine hydrochloride (2.1 g, 30 mmol), potassium carbonate (2.2 g, 16 mmol) and water (5 mL) was stirred for 30 min at rt and then at reflux temperature for 3 h. The reaction mixture was left at rt for 2 days and then the solid formed was isolated by filtration. The solid was dried, boiled with ethanol (200 mL) and filtered hot to remove inorganic impurities. The filtrate was evaporated to give 2.0 g (76%) of N-hydroxy-6-(4-isopropylpiperazin-1-yl)nicotinamidine.

Workup

  1. temperatureat reflux temperature for 3 h
  2. waitThe reaction mixture was left at rt for 2 days
  3. customthe solid formed
  4. customwas isolated by filtration
  5. customThe solid was dried
  6. filtrationfiltered hot
  7. customto remove inorganic impurities
  8. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-93ce3cc02655456bae14f01d11d5a94d
Source dataset
uspto-grants-2014_09
Patent number
US08846677B2

Reaction notes

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