Hydroxyamine hydrochloride → N'-Hydroxy-5-indanylethanimidamide

HRID 330294Notes

Reaction equation

HRID 330294 reaction equation
C[O-].[Na+].Cl.[NH2:5][OH:6].[CH2:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][C:17]#[N:18])=[CH:13][CH:14]=2)[CH2:9][CH2:8]1>CO>[OH:6][N:5]=[C:17]([NH2:18])[CH2:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[CH2:7][CH2:8][CH2:9]2

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 148193682-(2,3-dihydro-1H-inden-5-yl)acetonitrile

Product 1

HCID 54070119N'-Hydroxy-5-indanylethanimidamideYield 54.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred mixture of NaOMe (25 wt % in MeOH, 16.0 mL, 0.070 mol), hydroxylamine hydrochloride (4.9 g, 0.070 mol), and MeOH (60 mL) was heated under reflux for 30 minutes. 5-Indanylacetonitrile (10.0 g, 0.063 mol) was added and heating was continued for 18 hours. The mixture was cooled, concentrated, and partitioned between H2O and ether. The organic phase was dried (MgSO4) and concentrated to give a yellow oil: 11.4 g. The crude product was purified by flash chromatography (eluant 20% EtOAc/hexane; 60% EtOAc/hexane) and recrystallized from ether/hexane to give 6.5 g (54%) of a pale yellow solid, m.p. 60° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureheating
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. custompartitioned between H2O and ether
  7. dry with materialThe organic phase was dried (MgSO4)
  8. concentrationconcentrated
  9. customto give a yellow oil
  10. customThe crude product was purified by flash chromatography (eluant 20% EtOAc/hexane; 60% EtOAc/hexane)
  11. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-c997883f71094f0086992e46499a6ec8
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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