ChemicalBook CAS DataBase List (1H-INDAZOL-3-YL)-ACETIC ACID

(1H-INDAZOL-3-YL)-ACETIC ACID synthesis

8synthesis methods

Product Name:(1H-INDAZOL-3-YL)-ACETIC ACID
CAS Number:26663-42-3
Molecular formula:C9H8N2O2
Molecular Weight:176.17

5678-48-8

26663-42-3

The general procedure for the synthesis of indazole-3-acetic acid from 3-amino-3-(2-nitrophenyl)propionic acid was as follows: 3-amino-3-(2-nitrophenyl)propionic acid (15 g, 71.4 mmol) was dissolved in a mixture of 5% sodium hydroxide solution (85 mL) and 85% hydrazine hydrate (5 mL). The reaction mixture was heated to 80°C, followed by the slow addition of nickel ruanne (25 mg in two portions). After the reaction was carried out for half an hour, the reaction mixture was cooled and the pH was adjusted to ≈2 with 6 N hydrochloric acid.The precipitated solid precipitate was collected by filtration and dried under vacuum to give 6.86 g of yellow solid product in 54.5% yield.

5678-48-8 Synthesis

5678-48-8
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$43.50/5g

26663-42-3
87 suppliers
$73.00/100mg

Yield:26663-42-3 78%

Reaction Conditions:

with hydrazine hydrate;sodium hydroxide in water at 80; for 0.5 h;

Steps:

3.10.7. 2-(1. H-indazol-3-yl)acetic Acid (7)

The compound 6 (502 mg, 2.4 mmol) was dissolved in 2.8 mL of aqueous solution of 5% NaOHand then 98% hydrazine hydrate (160 L) was added. The reaction was heated to 80 °C, and Raney nickel (5 mg) reduction was carried out. After 30 min, the reaction mixture was cooled and adjustedto a pH of 2 with concentrated HCl. The precipitated solid was filtered o and dried over NaOH indesiccator to obtain the compound 8 (329.9 mg, 78%). TLC (CH2Cl2:MeOH, 3:1 v/v): Rf = 0.53; 1H NMR(CD3OD, 400 MHz): δ 7.76-7.71 (m, 1H), 7.47 (d, J = 8.5 Hz, 1H), 7.39-7.33 (m, 1H), 7.12 (t, J = 7.5 1H),3.98 (s, 2H); MS: for C9H9N2O2 (M + H+) m/z 176.1 found; 176.1 calculated.

References:

?kach, Kry?tof;Dostálková, Al?běta;Flegel, Martin;Hadravová, Romana;Hrabal, Richard;K?í?ová, Ivana;Kaufman, Filip;Ruml, Tomá?;Rumlová, Michaela [Molecules,2020,vol. 25,# 8]

141-82-2 Synthesis