Water → 5,6,7,8-Tetrahydro-7-(methylamino)quinoline

HRID 1461292노트

반응식

HRID 1461292 반응식
[Cl-].[CH3:2][NH3+:3].[N:4]1[C:13]2[CH:12]=[CH:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.O.[OH-].[Na+]>CO.[Cl-].[Na+].O.C(OCC)(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][NH:3][CH:11]1[CH2:12][C:13]2[N:4]=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:9][CH2:10]1

참가 물질

9

반응물 4

HCID 962WaterHCID 11637Methanamine, hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 123183175,6-Dihydroquinoline

생성물 1

HCID 148359215,6,7,8-Tetrahydro-7-(methylamino)quinoline수율 83.2%

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 8857Ethyl Acetate용매HCID 21584019Toluene ethylacetate용매HCID 57417360Sodium chloride; water용매

실험 절차

A solution of methylammonium chloride (1.35 g, 20 mmol) in methanol (2 ml) was added to 5,6-dihydroquinoline (1.31 g, 10 mmol) in methanol (2 ml) and the solution was heated under reflux for 21h, poured onto a mixture of water (25 ml) and brine (25 ml), and basified with 10N-NaOH (25 ml). The mixture was extracted with chloroform (3×25 ml), and the extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil. Chromatography [alumina; ethyl acetate-toluene (1:4)→ethyl acetate] gave the product (1.35 g) as an oil which was identical to the compound isolated in Example 2.

후처리

  1. temperaturethe solution was heated
  2. extractionThe mixture was extracted with chloroform (3×25 ml)
  3. dry with materialthe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil

출처 및 근거

ORD 기록
ord-8fed0ceb97524b93b7d35b54634c528a
출처 데이터셋
uspto-grants-1991_12
특허 번호
US05075303

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