ChemicalBook CAS DataBase List 1-pentyl-1H-indole-3-carboxylic acid

1-pentyl-1H-indole-3-carboxylic acid synthesis

7synthesis methods

Product Name:1-pentyl-1H-indole-3-carboxylic acid
CAS Number:727421-73-0
Molecular formula:C14H17NO2
Molecular Weight:231.29

1338925-20-4 Synthesis

1338925-20-4
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$103.00/1mg

727421-73-0
41 suppliers
$39.00/1mg

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 Synthesis