Dimethylformamide → 1-(4-Butylbenzyl)isoquinoline

HRID 604772노트

반응식

HRID 604772 반응식
CN(C)C=O.[H-].[Na+].[C:8]([CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]1C(=O)C1C=CC=CC=1)#N.[CH2:28]([C:32]1[CH:39]=[CH:38][C:35](CCl)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]>O>[CH2:28]([C:32]1[CH:39]=[CH:38][C:35]([CH2:8][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][N:11]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]

참가 물질

6

반응물 4

HCID 6228Dimethylformamide2회HCID 24758Sodium hydrideHCID 182273Benzene, 1-butyl-4-(chloromethyl)-HCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile

생성물 1

HCID 99002251-(4-Butylbenzyl)isoquinoline수율 17.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a dimethylformamide (1.8 ml) solution of 60% sodium hydride (16 mg, 0.40 mmol), a dimethylformamide (3.6 ml) solution of 1-cyano-2-benzoyl-1,2-dihydroisoquinoline (100 mg, 0.38 mmol) synthesized according to the literature of Org. Synth., VI, 115(1988), and 4-n-butylbenzylchloride (70 mg, 0.38 mmol) was added dropwise under nitrogen atmosphere at −16° C., and was further stirred at room temperature for 30 minutes. Water was added, this was concentrated, and toluene and water were added to this residue. The toluene layer was washed with water, dried over potassium carbonate, and concentrated. To an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added, and this was refluxed for 2 hours. After concentration, toluene and water were added. The toluene layer was washed with water, then dried over calcium carbonate, and then concentrated. The residue was purified by silica gel column chromatography to give 18 mg of the aforementioned compound of the formula (Ia).

후처리

  1. concentrationthis was concentrated
  2. additiontoluene and water were added to this residue
  3. washThe toluene layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. additionTo an ethanol (1.6 ml) solution of the residue, 50% aqueous sodium hydroxide solution (0.63 ml) was added
  7. temperaturethis was refluxed for 2 hours
  8. concentrationAfter concentration, toluene and water
  9. additionwere added
  10. washThe toluene layer was washed with water
  11. dry with materialdried over calcium carbonate
  12. concentrationconcentrated
  13. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-14ceab7d0d324a6b88cd8bf5d8bf99d9
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910712B2

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