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6-bromo-2,3,4,9-tetrahydro-carbazol-1-one oxime[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
100%
With pyridine; hydroxylamine hydrochloride; In ethanol; for 1h;Heating / reflux;
Compound 41 is prepared from Compound 1 as follows. Pyridine (5.64 ml, 39.8 mmol) is added to a mixture of Compound 1 (5.25g, 19.9 mmol) and hydroxylamine HCl salt (2.76g, 39.8 mmol) in ethanol (EtOH). The mixture is refluxed for about 1 h, and the solids are dissolved upon heating. The reaction mixture is then concentrated to dryness. The resulting sticky solid is treated and washed with hexanes (3x) to give a tan colored power of Compound 41, 6.1g, 100%
With hydrogenchloride; acetic acid; In water; for 3h;Heating / reflux;
Example 2; Preparation of 6-bromo-N-cyclohexyl-2, 3,4, 9-tetrahydro-lH-carbazol-1-amine; a) 6-bromo-2,3, 4, 9-tetrahydro-1H-carbazol-1-one; [0105] To a round bottom flask was added 4-bromoaniline and concentrated aqueous HCl (5.8 eq). Once the mixture was cooled to 0C using an ice bath, a solution of sodium nitrite (1 eq) in water was slowly added over 30 min. The reaction was then maintained at 0C for 1 hour. A mixture of 2- (hydroxymethylene) cyclohexan-l-one (1. 5eq), sodium acetate (2.3 eq), methanol, and water was added to the above diazotized solution over 10 minutes. After stirring at 0C for 1 hour, the pure product was filtered from the reaction and washed with water. Vacuum suction was maintained overnight to yield the crude intermediate that was then mixed with concentrated aqueous HCl (5.8 eq) in glacial acetic acid and heated to reflux for 3 hours. The resulting mixture was allowed to cool to room temperature. The reaction was diluted with water (3 times the reaction volume) and the resulting slurry was extracted with ethyl acetate (4x). The organic layers were combined and dried over sodium sulfate. The resulting filtrate solution was concentrated ifz vacuo to yield the crude product, which was purified via flash chromatography using hexanes/ethyl acetate. The pure fractions were combined and concentrated ii ? vacito to yield 6-bromo-2,3, 4, 9-tetrahydro-lH-carbazol-l-one as a solid (LC/MS MH+ 264.0, Rt 2.81 min).
Chemistry
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