ChemicalBook CAS DataBase List 2-ACETAMINO-4-CHLOROTOLUENE

2-ACETAMINO-4-CHLOROTOLUENE synthesis

9synthesis methods

Product Name:2-ACETAMINO-4-CHLOROTOLUENE
CAS Number:5900-55-0
Molecular formula:C9H10ClNO
Molecular Weight:183.64

89-59-8 Synthesis

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Yield:5900-55-0 94%

Reaction Conditions:

Stage #1: 4-chloro-2-nitrotoluenewith sodium tetrahydroborate in water at 60 - 70;Green chemistry;
Stage #2: acetic anhydride in water at 60 - 70;Green chemistry;

Steps:

A typical procedure for reductive-acetylation of nitrobenzene

General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of nitrobenzene (0.123 g, 1 mmol) and H2O(2 mL) was prepared. Fe3O4SiO2Cu-Ni-Fe-CrLDH (10 mg) was then added and the mixture was stirred for 5 min. Next, NaBH4 (0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min at 60-70 °C. TLC monitored the progress of the reaction (eluent, n-hexane / EtOAc: 5/2). Ac2O (0.102 g, 1 mmol) was then added and the reductive-acetylation was occurred immediately at 60-70 °C. After formation of acetanilide, the core-shell nanocatalyst was separated by an external magnet and the reaction mixture was extracted with EtOAc(2 × 5 mL). The organic layer was dried over anhydrous Na2SO4 followed by evaporation of the solvent to afford pure acetanilide in 96% yield (Table 4, entry 1).

References:

Gilanizadeh, Masumeh;Zeynizadeh, Behzad [Journal of the Iranian Chemical Society,2018,vol. 15,# 12,p. 2821 - 2837]

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