Synthesis Of N-(2-methoxy-5-nitrophenyl) Acetamide

The synthesis of N-(2-methoxy-5-nitrophenyl) acetamide was investigated in this dissertation.2,4-Dinitrochlorobenzene was used as starting material,and treated by methoxylation,selective reduction and acylation to afford N-(2-methoxy-5-nitrophenyl) acetamide.Phase transfer catalyst for methoxylation was carefully selected,and reducing agents for selective reduction were investigated.The influence of the reaction conditions on the yield of N-(2-methoxy-5-nitrophenyl) acetamide was studied.The mechanistic aspects of these reactions were also discussed.The optimal conditions for the reactions were summarized as follows:(1) In the presence of PEG-4000 as phase transfer catalyst,the methoxylation could be run smoothly at 60℃for 0.5 h,and the ratio of n(2,4-dinitrochlorobenzene):n(NaOH):n(CH₃OH): n(PEG-4000) was 1:1.1:12:0.00025.(2) When the molar ratio of sodium disulfide to 2, 4-dinitroanisole was 1.3,and the molar ratio of methanol to 2,4-dinitroanisole was 10,the selective reduction of 2,4-dinitroanisole could be finished at 60℃within 0.5 h to afford 2-amino-4-nitroanisole.(3) N-acylation was carried out using acetic acid and acetic anhydride as acylating agent with 2-amino-4-nitroanisole at 70℃for 1 h,and the ratio of n(2-amino-4-nitroanisole):n(acetic acid):n(acetic anhydride) was 1:3.5:1.5.The overall yield of N-(2-methoxy-5-nitrophenyl) acetamide was 77.64%,and the purity of the product was up to 99.17%.