ChemicalBook CAS DataBase List [3-(4-CHLOROPHENYL)-5-ISOXAZOLYL]METHANAMINE

[3-(4-CHLOROPHENYL)-5-ISOXAZOLYL]METHANAMINE synthesis

7synthesis methods

Product Name:[3-(4-CHLOROPHENYL)-5-ISOXAZOLYL]METHANAMINE
CAS Number:66046-42-2
Molecular formula:C10H9ClN2O
Molecular Weight:208.64

(NE)-N-[(4-chlorophenyl)methylidene]hydroxylamine

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2450-71-7 Synthesis

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[3-(4-CHLOROPHENYL)-5-ISOXAZOLYL]METHANAMINE

66046-42-2
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Yield:66046-42-2 62%

Reaction Conditions:

Stage #1: 4-chlorobenzaldehyde oximewith N-chloro-succinimide in dichloromethane; for 0.333333 h;Heating / reflux;
Stage #2: Propargylaminewith triethylamine in dichloromethane; for 2 h;Heating / reflux;

Steps:

4; 13 Preparation of 3-p-chlorophenyl-5-aminomethyl-isoxazole.

Example 4 Preparation of 3-p-chlorophenyl-5-aminomethyl-isoxazole. 1.56 g (10mmol) of p-chlorobenzaldoxime was dissolved in 40ml of dried dichloromethane in a erlenmeyer flask equipped with a magnetic stirrer, and 1.7 g (12mmol) of N-chlorosuccinimide was added slowly. The reaction mixture was stirred until completely dissolved. The system was heated slightly for 20 min. Then, 0.56 g (10mmol) of propargyl amine was introduced and 1.2 g (12mmol) of triethylamine was added dropwise, which caused the emission of white smog. The reaction mixture was heated under reflux for 2 h, and then purified by column chromatography on silica gel using petroleum ether (b.p. 60-90°C) - ethyl acetate (v:v = 4:1) as eluant, to obtain 2.3 g of the product as yellow solid. The yield was 62%. ¹H NMR (CDCl₃), δ (ppm): 2.8 (s), 1H; 4.8 (s), 2H; 6.5 (s), 1H; 7.2-7.8 (m), 4H.

References:

EP1935892,2008,A1 Location in patent:Page/Page column 10