Potassium Hydroxide → HCID 88831731, compound

HRID 268095Notes

Reaction equation

HRID 268095 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=1)([O-:3])=[O:2].[OH-:17].[K+].[ClH:19].[NH2:20]O>C(O)(C)C>[ClH:19].[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[O:14][C:13]([C:15](=[N:20][OH:17])[NH2:16])=[CH:12][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 7385205-(2-Nitrophenyl)-2-furonitrile

Product 1

HCID 88831731HCID 88831731, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 5-(2-nitrophenyl)-2-furonitrile (34 g, 0.16 mole), KOH (9.5 g, 0.17 mole), hydroxylamine hydrochloride (11.5 g, 0.165 mole) and absolute alcohol (400 ml) was heated under reflux for 2 hours. The reaction mixture was cooled in ice, and the insoluble material was collected by filtration. The solvent was removed on a rotary evaporator, and the residual oil (44 g) was triturated with water several times. It was dissolved in anhydrous ether (ca. 2l. ) and the insoluble material was removed by filtration. Gaseous HCl was introduced into the filtrate yielding a solid that was collected by filtration and washed with anhydrous ether to give 33 g (73%). An analytical sample, m.p. 205°-206°, was obtained by recrystallization from isopropanol.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was cooled in ice
  4. filtrationthe insoluble material was collected by filtration
  5. customThe solvent was removed on a rotary evaporator
  6. customthe residual oil (44 g) was triturated with water several times
  7. dissolutionIt was dissolved in anhydrous ether (ca. 2l. )
  8. customthe insoluble material was removed by filtration
  9. additionGaseous HCl was introduced into the filtrate
  10. customyielding a solid
  11. filtrationthat was collected by filtration
  12. washwashed with anhydrous ether
  13. customto give 33 g (73%)

Sources & evidence

ORD record
ord-9adc6ad961704a24991337b146cc1e8f
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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