Water → 2-(2-Aminophenyl)-2,3-dihydro-1H-indole

HRID 373834

Reaktionsgleichung

Reaktionsgleichung von HRID 373834
C([BH3-])#N.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[NH:13][C:14]2[C:19]([CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.O>CC(O)=O>[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 7359662-(2-Aminophenyl)indoleHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 197614202-(2-Aminophenyl)-2,3-dihydro-1H-indoleAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Sodium cyanoborohydride (6.4 g) was added in several portions to a solution of 6.0 g 2-(2-aminophenyl)-1H-indole in 200 ml HOAc at 5° C. The resulting solution was stirred at room temperature overnight. Water was added and the reaction mixture was concentrated. The residue was diluted with ice water and made basic with 50% NaOH. This mixture was extracted with Et2O and the extracts were washed with water and saturated NaCl solution, and dried (MgSO4). Concentration gave 6.1 g crude product which was chromatographed by HPLC to give 3.05 g solid, m.p. 115°-117° C.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. additionThe residue was diluted with ice water
  3. extractionThis mixture was extracted with Et2O
  4. washthe extracts were washed with water and saturated NaCl solution
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration
  7. customgave 6.1 g crude product which
  8. customwas chromatographed by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-39c031d9a1c24f2885879d80cceb81be
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166170

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