1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE synthesis
- Product Name:1-(3-HYDROXY-PROPYL)-1H-INDOLE-3-CARBALDEHYDE
- CAS Number:351015-67-3
- Molecular formula:C12H13NO2
- Molecular Weight:203.24
Yield:351015-67-3 86%
Reaction Conditions:
Stage #1: Indole-3-carboxaldehydewith potassium hydroxide in dimethyl sulfoxide at 20; for 1 h;Inert atmosphere;
Stage #2: 1-chloro-3-hydroxypropane in dimethyl sulfoxide at 20; for 5 h;Inert atmosphere;
Steps:
1 4.3.3 1-(3-Hydroxypropyl)-1H-indole-3-carbaldehyde (12)
General procedure: To a solution of DMSO (10ml) taken in a round bottom flask was added KOH (2equiv) and the solution was stirred at room temperature for 15min. The indole derivative 2 or 7 (1equiv) was then added and the mixture was further stirred for 1h, after which 4-chlorobutan-1-ol or 3-chloropropan-1-ol (1.5equiv) was added dropwise to the reaction mixture. The reaction was monitored by TLC to completion within 5h. The reaction mixture was then quenched by adding water and was extracted with ethyl acetate. Evaporation of the solvent under reduced pressure followed by column chromatography gave the required N-alkylated compounds, 3/8/12/16.
References:
Naik, Prajakta N.;Naik, Nilesh H.;Khan, Ayesha;Kusurkar, Radhika S. [Tetrahedron,2013,vol. 69,# 32,p. 6545 - 6551]
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