Ethanol → HCID 178456338, compound

HRID 1887135Notes

Reaction equation

HRID 1887135 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-e70b456bfc5f49d4a79d9b85be819bff
Source dataset
uspto-grants-2013_08
Patent number
US08501739B2

Reaction notes

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