Acetic Acid → 4-(2-amino-4,5-dimethylphenoxymethyl)-3-methylbenzoic Acid Methyl Ester

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Reaktionsgleichung

[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[N+:20]([O-])=O)=[C:6]([CH3:23])[CH:5]=1.C(O)(=O)C>[Fe].O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]2[CH:17]=[C:16]([CH3:18])[C:15]([CH3:19])=[CH:14][C:13]=2[NH2:20])=[C:6]([CH3:23])[CH:5]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

A mixture of 4-(2-nitro-4,5-dimethylphenoxymethyl)-3-methylbenzoic acid methyl ester prepared in Reference Example 1 (7.21 g), acetic acid (88 ml) and water (8.8 ml) was stirred at 50° C. To the reaction solution, iron powder (6.11 g) was gradually added, and the mixture was stirred for 1 hour at 50° C. After cooling, the mixture was filtered and the filtrate was concentrated and azeotroped with toluene. To the residue, ethyl acetate-water (100 ml-100 ml) was added and the mixture was filtrated over Celite (registered trademark). The organic layer was washed, dried, concentrated under reduced pressure to give the title compound (4.66 g) having the following physical data.

Aufarbeitung

stirringthe mixture was stirred for 1 hour at 50° C
temperatureAfter cooling
filtrationthe mixture was filtered
concentrationthe filtrate was concentrated
customazeotroped with toluene
additionTo the residue, ethyl acetate-water (100 ml-100 ml) was added
filtrationthe mixture was filtrated over Celite (registered trademark)
washThe organic layer was washed
customdried
concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-c507ecb755b542f3a3ddc3822845d926
Quelldatensatz: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07629369B2

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