Anthranilic Acid → N-Methylanthranilic acid

HRID 1380677

Reaktionsgleichung

Reaktionsgleichung von HRID 1380677
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH2:11]=O.[H][H]>>[CH3:11][NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9]

Komponenten

4

Versuchsvorschrift

At least two processes for the preparation of the subject compound are known in the prior art. In one such process anthranilic acid is used as the starting compound and reacted with formaldehyde and hydrogen as described in J. Soc. Org. Synthetic Chem. (Japan) 11,434 (1953), Chem. Abst. 49, 955a (1955), to produce N-methylanthranilic acid. This resulting intermediate is thereafter reacted with thionyl chloride and methanol to produce the desired methyl N-methylanthranilate. This step is described in Aust. J. Chem. 27, 537 (1974). The disadvantages of this process lie in the use of a relatively expensive starting material and the relatively poor yields of final product. Typical reported reaction yields based on the starting compound amount to about 36% overall for the two steps.

Aufarbeitung

  1. customAt least two processes for the preparation of the subject compound

Quellen und Nachweise

ORD-Eintrag
ord-3818787d25e649d68cc025fc8c94109e
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04582922

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