Potassium Hydroxide → HCID 13958990, compound

HRID 255855Notes

Reaction equation

HRID 255855 reaction equation
Cl.N[OH:3].[OH-].[K+].[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]#[N:17])=[CH:8][N:7]=1>C(O)C>[N:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]([NH2:17])=[O:3])=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 5932574-Cinnolinecarbonitrile

Product 1

HCID 13958990HCID 13958990, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.76 g of hydroxylamine hydrochloride was added to a stirred solution of 0.72 g of 85% aqueous potassium hydroxide in 25 ml of absolute ethanol at room temperature. The mixture was stirred at room temperature for 20 minutes, then 1.55 g of 27C was added and the mixture was heated at reflux for 3 hours, held overnight at room temperature, and filtered. The filtrate was stripped of solvent to give a dark oil, from which a yellow solid precipitated on standing. The solid was separated, and stirred in hot ethyl acetate. The resulting mixture was filtered, the solvent was stripped from the filtrate and the residue was recrystallized from ethanol to give 27, as a yellow solid, m.p.: 223° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 hours
  3. waitheld overnight at room temperature
  4. filtrationfiltered
  5. customto give a dark oil
  6. customfrom which a yellow solid precipitated
  7. customThe solid was separated
  8. stirringstirred in hot ethyl acetate
  9. filtrationThe resulting mixture was filtered
  10. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-13437b95c4ef4531a91bcb2765312a37
Source dataset
uspto-grants-1987_10
Patent number
US04699651

Reaction notes

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