1-pentyl-1H-indole-3-carboxylic acid synthesis
- Product Name:1-pentyl-1H-indole-3-carboxylic acid
- CAS Number:727421-73-0
- Molecular formula:C14H17NO2
- Molecular Weight:231.29
1338925-20-4
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727421-73-0
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Yield:727421-73-0 92%
Reaction Conditions:
Stage #1: methyl 1-pentyl-1H-indole-3-carboxylatewith potassium hydroxide in ethanol;water at 20 - 75;
Stage #2: with hydrogenchloride in ethanol;water;
Steps:
5.1.14. N-(Naphthalen-2-yl)-1-pentyl-1H-indole-3-carboxamide (18)
Step 1. To a solution of 34 (2.34 g, 9.44 mmol) in 45 mL EtOH was added dropwise a solution of KOH (85%, 1.87 g, 28.33 mmol) in 5 mL H2O, and the resulting mixture was stirred overnight at ambient temperature. Hereafter, an additional portion of KOH (85%, 1 g) was added and the mixture was successively heated to 75 °C for 4 h, acidified with 1 M HCl (2 × 25 mL) and extracted with Et2O ( × 3). Residual water and EtOH was removed in vacuo with CH3CN as azeotrope ( × 4), additional concentration in vacuo gave 1-pentyl-1H-indole-3-carboxylic acid (2.11 g, 92% yield). 1H NMR (400 MHz, CDCl3) δ 8.27-8.20 (m, 1H), 7.93 (s, 1H), 7.42-7.37 (m, 1H), 7.33-7.28 (m, 2H), 4.17 (t, J = 7.2 Hz, 2H), 1.94-1.85 (m, 2H), 1.38-1.30 (m, 4H), 0.90 (t, J = 6.9 Hz, 3H).
References:
Blaazer, Antoni R.;Lange, Jos H.M.;Van Der Neut, Martina A.W.;Mulder, Arie;Den Boon, Femke S.;Werkman, Taco R.;Kruse, Chris G.;Wadman, Wytse J. [European Journal of Medicinal Chemistry,2011,vol. 46,# 10,p. 5086 - 5098] Location in patent:experimental part
771-50-6
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110-53-2
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727421-73-0
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727421-73-0
48 suppliers
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727421-73-0
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120-72-9
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727421-73-0
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