Hydrochloric Acid → 5-(3-Aminophenyl)pent-4-yn-1-ol

HRID 1944876노트

반응식

HRID 1944876 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]#[C:11][CH2:12][CH2:13][CH2:14][OH:15])[CH:7]=[CH:8][CH:9]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 575169425-(3-Nitrophenyl)pent-4-yn-1-ol

생성물 1

HCID 575169435-(3-Aminophenyl)pent-4-yn-1-ol

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

실험 절차

A solution of Intermediate 46 (16 mmol) in ethanol (80 mL) was treated successively with 10% aqueous hydrochloric acid solution (4 mL) and iron powder and then was lowered in to a 95° C. oil bath. After 90 minutes of reflux heating, the mixture was deemed complete by LC/MS analysis and was filtered while hot through a pad of Celite diatomaceous earth, eluting with methanol. The filtrate was concentrated to dryness under reduced pressure. The residue was purified via automated flash silica gel chromatography, using a 40 g Silicycle SiliSep flash column (hexanes/ethyl acetate). Concentration of the desired fractions under reduced pressure provided the title compound. ES/MS calcd. for C11H14NO+ 176.1. Found m/z=176.2 (M+H)+.

후처리

  1. customwas lowered in to a 95° C. oil bath
  2. temperatureAfter 90 minutes of reflux
  3. temperatureheating
  4. filtrationwas filtered while hot through a pad of Celite diatomaceous earth
  5. washeluting with methanol
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customThe residue was purified via automated flash silica gel chromatography

출처 및 근거

ORD 기록
ord-b0c73cb86fd84460b599244ecff832eb
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394829B2

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