N-benzoyl-1,2-dihydroquinolin-4(3H)-one → N-benzoyl-1,2,3,4-tetrahydroquinolin-4-ol

HRID 1097783Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1097783
[BH4-].[Na+].[C:3]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](=[O:21])[CH2:13][CH2:12]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[OH:21][CH:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:11]([C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:10])[CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 283524N-benzoyl-1,2-dihydroquinolin-4(3H)-oneHCID 4311764Sodium borohydride

Produkt 1

HCID 59277722N-benzoyl-1,2,3,4-tetrahydroquinolin-4-olAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

NaBH4 (85 mg, 2.25 mmol) is added to a solution of 1-benzoyl-2,3-dihydro-1H-quinolin-4-one (from step C) in methanol (5 mL) at 0° C. The resulting mixture is stirred at room temperature. After 1 h, the reaction is quenched by 1 N HCl. The solvent is removed under vacuum. The residue is taken up in CH2Cl2 and washed by brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by flash chromatography to give the title compound (380 mg, 84.8% yield for the two steps).

Aufarbeitung

  1. customthe reaction is quenched by 1 N HCl
  2. customThe solvent is removed under vacuum
  3. washwashed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-524e56e28f8d4ae6bd17bd4c79a6b74d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143278B2

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