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

HRID 1866201Notes

Reaction equation

[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

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-c507ecb755b542f3a3ddc3822845d926
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629369B2

Reaction notes

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