ChemicalBook CAS DataBase List 2-[(7-CHLORO-4-QUINOLINYL)SULFANYL]ACETIC ACID

2-[(7-CHLORO-4-QUINOLINYL)SULFANYL]ACETIC ACID synthesis

4synthesis methods

Product Name:2-[(7-CHLORO-4-QUINOLINYL)SULFANYL]ACETIC ACID
CAS Number:5429-07-2
Molecular formula:C11H8ClNO2S
Molecular Weight:253.7

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2-[(7-CHLORO-4-QUINOLINYL)SULFANYL]ACETIC ACID

5429-07-2
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$66.00/1g

Yield:5429-07-2 93%

Reaction Conditions:

with sodium hydroxide in water at 60; for 1 h;

Steps:

Synthesis of 2-(7-chloroquinolin-4-ylthio)acetic acid (3)

A mixture of compound 2 (3.0 mmol) in aqueous 1N NaOH 5 mL was heated to 60°C with constant agitation for 1 h. Following completion of the reaction, it was cooled and acidified with 10% HCl until it reached pH=3. The white solid obtained was filtered and washed with water and diethyl ether. The obtained solid was recrystallized using ethanol. Yield 93%, m.p.: 210°C (decomposition) (lit. 228-229).33 IR ν (cm-1): 1699 (C=O). 1H NMR (270MHz DMSO-d6): δ 4.18 (s, 2H, H-2′), 7.39 (d, 1H, J3-2=4.9 Hz, H-3), 7.68 (dd, 1H, J6-8=2.2Hz, J6-5=9.1 Hz, H-6), 8.06 (d, 1H, J8-6=1.4 Hz, H-8), 8.11 (d, 1H, J5-6=9.1 Hz, H-5), 8.75 (d, 1H, J2-3=4.94 Hz, H-2). 13C NMR (67.9MHz DMSO-d6): δ 33.5, 117.5, 124.7, 125.8, 127.8, 128.8, 135.1, 146.8, 147.9, 151.3, 170.1. Anal. calcd for C11H8ClNO2S: C, 52.08; H, 3.18; N, 5.52; found: C, 51.97; H, 3.17; N, 5.73.

References:

Colmenarez, Custodiana;Acosta, María;Rodríguez, Miguel;Charris, Jaime [Journal of Chemical Research,2020,vol. 44,# 3-4,p. 161 - 166]

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