Hydroxyamine hydrochloride → N'-Hydroxy-5-indanylethanimidamide

HRID 330294노트

반응식

HRID 330294 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c997883f71094f0086992e46499a6ec8
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04895860

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