2-bromo-5,6,7,8,9,10-hexahydrocyclohepta[b]indole synthesis
- Product Name:2-bromo-5,6,7,8,9,10-hexahydrocyclohepta[b]indole
- CAS Number:109160-55-6
- Molecular formula:C13H14BrN
- Molecular Weight:264.16
Yield: 88%
Reaction Conditions:
with Amberlite IR 120 in ethanol at 80; for 10 h;Fischer Indole Synthesis;
Steps:
EXPERIMENTAL
General procedure: A mixture of the carbonyl compound (5, 1.0 mmol), arylhydrazine (6, 1.2 mmol), and the solid acid (7, Amberlite, 1.5 g, obtained from Aldrich Chemical Co.) was refluxed in absolute ethanol (10 ml) for 8 h. The reaction was monitored by thin-layer chromatography(TLC), and upon completion the mixture was cooled to room temperature, the catalyst filtered off, and the product was washed thoroughly with ethylacetate (30 ml). The combined organics were washed with water, dried (Na2SO4), and concentrated in vacuo. The resulting residue was chromatographed on a silicagel column eluting with ethylacetate-hexane mixtures to obtain the purified indole (8). This was fully characterized by infrared, 400-MHz 1H NMR, high-resolution mass spectrometry, and melting point (solids).
References:
Chandrasekhar, Sosale;Mukherjee, Somnath [Synthetic Communications,2015,vol. 45,# 8,p. 1018 - 1022] Location in patent:supporting information
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1000210-73-0
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109160-55-6
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