Hydroxyamine hydrochloride → HCID 54129445, compound

HRID 268094Notes

Reaction equation

HRID 268094 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15]#[N:16])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].O(C)[Na].[NH2:20][OH:21].Cl>CO>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[O:14][C:13]([C:15](=[N:20][OH:21])[NH2:16])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 215533215-(4-Acetylphenyl)furan-2-carbonitrileHCID 178418582HCID 178418582, compound

Product 1

HCID 54129445HCID 54129445, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 17.0 g (0.080) mole of 5-(4-acetylphenyl)-2-furonitrile, 4.24 g (0.080 mole) of NaOCH3 and 300 ml of anhydrous CH3OH was refluxed for 1 hour and then cooled to room temperature. After adding 5.16 g (0.080 mole) of NH2OH.HCl, the reaction was stirred at room temperature for 2 hours at near reflux for 15 minutes and then cooled in an ice bath. The resulting solid was filtered, air dried, and recrystallized from ethyl acetate/Darco to yield 4.5 g (23%). An analytical sample was prepared by drying a sample in the vacuum pistol at the temperature of refluxing CHCl3, m.p. 197°-199°.

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureat near reflux for 15 minutes
  3. temperaturecooled in an ice bath
  4. filtrationThe resulting solid was filtered
  5. customair dried
  6. customrecrystallized from ethyl acetate/Darco
  7. customto yield 4.5 g (23%)
  8. customAn analytical sample was prepared
  9. dry with materialby drying a sample in the vacuum pistol at the temperature of refluxing CHCl3, m.p. 197°-199°

Sources & evidence

ORD record
ord-d790717d92c140638dd6324a5405d2a7
Source dataset
uspto-grants-1976_03
Patent number
US03946049

Reaction notes

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