Benzaldehyde → 8-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline

HRID 18246

반응식

HRID 18246 반응식
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[CH:1](=[C:17]1[C:18]2[N:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 240BenzaldehydeHCID 663355,6,7,8-Tetrahydroquinoline

생성물 1

HCID 540746508-(Phenylmethylidene)-5,6,7,8-tetrahydroquinoline수율 58%

시약·촉매·용매 1

HCID 7918Acetic Anhydride용매

실험 절차

Benzaldehyde (3.59 mL, 35.30 mmole) was added to a solution of 5,6,7,8-tetrahydro-quinoline (4.70 g, 35.30 mmole) in acetic anhydride (25 mL), and the solution was heated to reflux under a nitrogen atmosphere. After overnight at reflux, the reaction was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes) to give the title compound (4.50 g, 58%) as a waxy yellow solid after drying in vacuo: MS (ES) m/e 222 (M+H)+.

후처리

  1. temperaturethe solution was heated
  2. temperatureto reflux under a nitrogen atmosphere
  3. temperatureAfter overnight at reflux
  4. concentrationthe reaction was concentrated in vacuo
  5. additionThe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. customThe residue was purified by flash chromatography on silica gel (33% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-567f86177836440aaa9b4f74f8fe4c87
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741339B2

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