Water → 5-Methoxy-2-(6-methoxy-3,4-dihydronaphthalen-2-yl)phenylamine

HRID 1433892Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[N+:21]([O-])=O)[CH2:9][CH2:10]2)=[CH:5][CH:4]=1.[Cl-].[NH4+].O>CO.[Fe]>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([C:8]2[CH2:9][CH2:10][C:11]3[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=3)[CH:7]=2)=[C:14]([NH2:21])[CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 7-methoxy-3-(4-methoxy-2-nitrophenyl)-1,2-dihydronaphthalene (600 mg), iron (430 mg) and ammonium chloride (830 mg) in methanol (15 ml) was added water (6 ml), and the solution was stirred for 6 hours at 80° C. The solution was filtered through celite pad, extracted with ethyl acetate, then sequentially washed with water and brine, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (356 mg).

Workup

filtrationThe solution was filtered through celite pad
extractionextracted with ethyl acetate
washsequentially washed with water and brine
customthe solvent was evaporated in vacuo
customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record: ord-f36de10e250b4648862e7063f0d62406
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612114B2

Reaction notes

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