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

HRID 415704Notes

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-f4773c9f1c1c4853919a369a9b3884fd
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088802B2

Reaction notes

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