N-甲基-N-甲酰基苯胺

N-甲基-N-甲酰基苯胺
別名	N-甲基甲酰苯胺; N-甲基-N-苯基甲酰胺
識別
CAS號	93-61-8
性質
熔點	13 °C（286 K）
沸點	243 °C（516 K）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

N-甲基-N-甲酰基苯胺是一種有機化合物，化學式為C₈H₉NO。它可由N-甲基苯胺（英語：N-Methylaniline）和甲酸在甲苯中回流反應製得，^[3]或由N,N-二甲基苯胺的氧化反應得到，氧化劑可選用雙氧水^[4]、2,2,6,6-四甲基-1-氧化哌啶鎓氯化物^[5]、苄基三乙基高錳酸銨^[6]、四乙基高碘酸銨^[7]等。它和三氯氧磷搭配可用於維爾斯邁爾－哈克反應。^[8]

參考文獻

^ H. B. Henbest, A. Thomas. 591. Amine oxidation. Part I. The side-chain oxidation of N-alkyl- and NN-dialkyl-anilines by manganese dioxide. Journal of the Chemical Society (Resumed). 1957: 3032 [2020-12-29]. ISSN 0368-1769. doi:10.1039/jr9570003032 （英語）.
^ Horner, Leopold; Betzel, Clemens. Course of substitutions. V. Experimental evidence of transitory radicals. Justus Liebigs Annalen der Chemie, 1953. 579. 175-192. ISSN: 0075-4617.
^ N-METHYLFORMANILIDE. Organic Syntheses. 1940, 20: 66 [2020-12-29]. doi:10.15227/orgsyn.020.0066. （原始內容存檔於2020-04-24）.
^ Yi-Dan Du, Chun-Wai Tse, Zhen-Jiang Xu, Yungen Liu, Chi-Ming Che. [Fe III (TF 4 DMAP)OTf] catalysed anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of methyl aryl tertiary amines to formamides with H 2 O 2 as a terminal oxidant. Chem. Commun. 2014, 50 (84): 12669–12672 [2020-12-29]. ISSN 1359-7345. doi:10.1039/C4CC05972G （英語）.
^ Duncan Harvey Hunter, Julie S. Racok, Allan W. Rey, Yolanda Zea-Ponce. Oxoiminium ions for N-demethylation: 1-oxo-2,2,6,6-tetramethylpiperidinium chloride. The Journal of Organic Chemistry. 1988-03, 53 (6): 1278–1281 [2020-12-29]. ISSN 0022-3263. doi:10.1021/jo00241a028 （英語）.
^ Schmidt, H. Juergen; Schaefer, Hans J. Oxidation of amines with benzyl(triethyl)ammonium permanganate. Angewandte Chemie, 1981. 93 (1): 124-125. ISSN: 0044-8249.
^ Dau. D. Agarwal, Daisy Bhat. Substituted tetraphenyl porphyrin catalyzed oxidative N-dealkylation of tertiary amine using molecular oxygen. Journal of Porphyrins and Phthalocyanines. 2016-06, 20 (06): 689–693 [2020-12-29]. ISSN 1088-4246. doi:10.1142/S1088424616500607 （英語）.
^ Petr Ilyin, Alena Pankova, Mikhail Kuznetsov. Direct and Efficient Synthesis of Pyrrole-3-carbaldehydes by Vilsmeier-Haack Formylation of Pyrroles with Sterically Crowded Amides. Synthesis. 2012-05, 44 (09): 1353–1358 [2020-12-29]. ISSN 0039-7881. doi:10.1055/s-0031-1290763. （原始內容存檔於2018-06-05）（英語）.

[1] H. B. Henbest, A. Thomas. 591. Amine oxidation. Part I. The side-chain oxidation of N-alkyl- and NN-dialkyl-anilines by manganese dioxide. Journal of the Chemical Society (Resumed). 1957: 3032 [2020-12-29]. ISSN 0368-1769. doi:10.1039/jr9570003032 （英語）.

[2] Horner, Leopold; Betzel, Clemens. Course of substitutions. V. Experimental evidence of transitory radicals. Justus Liebigs Annalen der Chemie, 1953. 579. 175-192. ISSN: 0075-4617.

[3] N-METHYLFORMANILIDE. Organic Syntheses. 1940, 20: 66 [2020-12-29]. doi:10.15227/orgsyn.020.0066. （原始內容存檔於2020-04-24）.

[4] Yi-Dan Du, Chun-Wai Tse, Zhen-Jiang Xu, Yungen Liu, Chi-Ming Che. [Fe III (TF 4 DMAP)OTf] catalysed anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of methyl aryl tertiary amines to formamides with H 2 O 2 as a terminal oxidant. Chem. Commun. 2014, 50 (84): 12669–12672 [2020-12-29]. ISSN 1359-7345. doi:10.1039/C4CC05972G （英語）.

[5] Duncan Harvey Hunter, Julie S. Racok, Allan W. Rey, Yolanda Zea-Ponce. Oxoiminium ions for N-demethylation: 1-oxo-2,2,6,6-tetramethylpiperidinium chloride. The Journal of Organic Chemistry. 1988-03, 53 (6): 1278–1281 [2020-12-29]. ISSN 0022-3263. doi:10.1021/jo00241a028 （英語）.

[6] Schmidt, H. Juergen; Schaefer, Hans J. Oxidation of amines with benzyl(triethyl)ammonium permanganate. Angewandte Chemie, 1981. 93 (1): 124-125. ISSN: 0044-8249.

[7] Dau. D. Agarwal, Daisy Bhat. Substituted tetraphenyl porphyrin catalyzed oxidative N-dealkylation of tertiary amine using molecular oxygen. Journal of Porphyrins and Phthalocyanines. 2016-06, 20 (06): 689–693 [2020-12-29]. ISSN 1088-4246. doi:10.1142/S1088424616500607 （英語）.

[8] Petr Ilyin, Alena Pankova, Mikhail Kuznetsov. Direct and Efficient Synthesis of Pyrrole-3-carbaldehydes by Vilsmeier-Haack Formylation of Pyrroles with Sterically Crowded Amides. Synthesis. 2012-05, 44 (09): 1353–1358 [2020-12-29]. ISSN 0039-7881. doi:10.1055/s-0031-1290763. （原始內容存檔於2018-06-05）（英語）.

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