Water → 2-Di-n-propylamino-8-(quinol-2-yl)-1,2,3,4-tetrahydronaphthalene

HRID 22139

반응식

HRID 22139 반응식
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[Mg].Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.O>C1COCC1.BrCCBr>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 119282-ChloroquinolineHCID 5462224MagnesiumHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

생성물 1

HCID 233735242-Di-n-propylamino-8-(quinol-2-yl)-1,2,3,4-tetrahydronaphthalene수율 181.9%

시약·촉매·용매 2

HCID 78391,2-Dibromoethane촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1 g, 3.22 mmol) was added to a refluxing mixture of magnesium turnings (120 mg, 4.9 mmol) in 50 ml THF. Formation of the Grignard reagent was initiated by addition of 0.2 ml 1,2-dibromoethane (0.002 mmol). After 1.5 hours, 220 mg (0.33 mmol) Ni[PPh3 ]2Cl2 in 10 ml of THF were added followed by 800 mg (4.89 mmol) of 2-chloroquinoline. The solution continued to reflux for 15 minutes after which it was cooled, poured into water, and extracted three times with methalene chloride. The extract was dried with sodium sulfate and concentrated to obtain 2.1 g of a black oil. The crude was purified by using two flash columns. The first was eluted with 1:1 hexanes:ether and the second with 20:1 methylene chloride:methanol. 130 mg of the title compound were collected as product. Following crystallization in ethanol and water, 66 mg of solid were recovered, m.p. 82° C. Analysis: Theory (.1/3 H2O): C, 82.37; H, 8.48; N, 7.68; Found: C, 82.33; H, 8.44; N, 7.73.

후처리

  1. temperatureto reflux for 15 minutes after which it
  2. temperaturewas cooled
  3. extractionextracted three times with methalene chloride
  4. dry with materialThe extract was dried with sodium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e52d946ba6b940f2adfefdb638da511e
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426226

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