Reaktion #985488

Reaktionsgleichung

hydrochloric acid

6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one

ammonium acetate

sodium cyanoborohydride

→

6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine

Ausbeute 52.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was cooled
2. 2
   SonstigeThe organics were removed under reduced pressure
3. 3
   Filtrationthe resulting precipitate was collected by filtration
4. 4
   workup.DISSOLUTIONdissolved in ethyl acetate
5. 5
   Waschenmethanol, and washed with saturated aqueous sodium carbonate
6. 6
   SonstigeThe phases were separated
7. 7
   Einengenthe organic phase was concentrated

Vorschrift

To a solution of to 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (500 mg, 2.3 mmol) and ammonium acetate (1.8 g, 23 mmol) in methanol (9 mL) was added sodium cyanoborohydride (720 mg, 11.5 mmol). After heating at 60° C. for 15 hours, the mixture was cooled and treated with concentrated hydrochloric acid until pH=1. The organics were removed under reduced pressure and the resulting precipitate was collected by filtration, dissolved in ethyl acetate and methanol, and washed with saturated aqueous sodium carbonate. The phases were separated and the organic phase was concentrated to yield 6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine (260 mg, 52% yield) as a light brown solid. 1H-NMR (DMSO-d6): δ 10.90 (s, 1H), 7.34 (m, 1H), 7.27 (d, 1H), 6.97 (dd, 1H), 3.90 (t, 1H), 2.54 (m, 2H), 2.04-1.89 (m, 2H), 1.66 (m, 1H), 1.50 (m, 1H); MS m/z 221 (M+1).

Quelle