Sodium Hydroxide → HCID 57079581, Verbindung

HRID 439843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 439843
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[C:11]4[C:16]([CH2:17][C:5]=3[C:4]=2[CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4.C([BH3-])#N.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C@@H:6]3[C:11]4[C:16]([CH2:17][C@@H:5]3[C:4]=2[CH:3]=1)=[CH:15][CH:14]=[CH:13][CH:12]=4

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 222470798-Methyl-5,10-dihydroindeno[1,2-b]indole

Produkt 1

HCID 57079581HCID 57079581, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

5,10-Dihydro-8-methylindeno[1,2-b]indole (10 g, 46 mmol) was stirred at room temperature in glacial acetic acid (150 cm3). Sodium cyanoborohydride (8.6 g, 3 equivalents) was added portionwise over a period of 30 minutes. The reaction was stirred for a further hour, and then poured into ice/water (200 cm3). After stirring for 30 minutes, the acidic solution was made basic by the addition of sodium hydroxide, and the colourless solid thus formed collected by filtration. This solid was washed copiously with water until the residue was free from cyanide ion, and then dried in a vacuum oven to yield the title compound as a colourless solid. Yield: 7.5 g (73%) M.p. 110° C. (from ethanol/water). 1H NMR (CDCl3) δ: 2.24 (3H, s,), 3.20 (1H, dd,), 3.50 (1H, dd,) 3.9 (1H, br,), 4.16 (1H, dd,), 5.23 (1H, d,), 6.52 (1H,d,), 6.80 (1H, d,), 6.99 (1H, s,), 7.1-7.4 (4H, m,).

Aufarbeitung

  1. stirringAfter stirring for 30 minutes
  2. customthe colourless solid thus formed
  3. filtrationcollected by filtration
  4. washThis solid was washed copiously with water until the residue
  5. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-ca0f4c6f72a8490da954a345f5cf53e7
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05516788

Notizen zur Reaktion

Wird geladen…