Dimethylformamide → 1-(4-Butylbenzyl)isoquinoline

HRID 1673074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673074
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]

Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 182273Benzene, 1-butyl-4-(chloromethyl)-HCID 2304882-Benzoyl-1,2-dihydro-1-isoquinolinecarbonitrile

Produkt 1

HCID 99002251-(4-Butylbenzyl)isoquinolineAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-11254bd120e0404e8d00a3ee98963ebe
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999090B2

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