Ethanol → 2-Methyl-1,2,3,4-tetrahydroquinoline

HRID 494188

반응식

HRID 494188 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[In].[Cl-].[NH4+].C(O)C>O>[CH3:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1

참가 물질

6

반응물 4

HCID 702EthanolHCID 70602-MethylquinolineHCID 25517Ammonium ChlorideHCID 5359967Indium

생성물 1

HCID 962892-Methyl-1,2,3,4-tetrahydroquinoline수율 63.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 2-methylquinoline (584 mg, 4.1 mmol), indium powder (4.21 g, 36.7 mmol), saturated aqueous ammonium chloride solution (6.3 ml) and ethanol (21 ml) were heated at reflux for 3 days. On cooling to room temperature, water was added and the mixture was filtered through Keiselguhr. The filtrate was adjusted to pH 9 with 2M sodium hydroxide solution and extracted with DCM (×2). The extracts were dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 10% EtOAc in 60-80C petroleum ether gave the title compound as a pale yellow oil (383 mg). 1H NMR (400 MHz, CDCl3) δ (ppm): 6.96 (m, 2H), 6.60 (t, 1H), 6.47 (d, 1H), 3.68 (br, 1H), 3.40 (m, 1H), 2.84 (ddd, 1H), 2.72 (ddd, 1H), 1.92 (m, 1H), 1.60 (m, 1H), 1.21 (d, 3H).

후처리

  1. temperaturewere heated
  2. temperatureat reflux for 3 days
  3. filtrationthe mixture was filtered through Keiselguhr
  4. extractionextracted with DCM (×2)
  5. dry with materialThe extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by flash column chromatography
  9. washElution with 10% EtOAc in 60-80C petroleum ether

출처 및 근거

ORD 기록
ord-5414c44d7deb413399c7c2cfc4a180f0
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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