ChemicalBook CAS DataBase List 4-tert-Butyl-3-methoxy-phenylamine

4-tert-Butyl-3-methoxy-phenylamine synthesis

6synthesis methods

Product Name:4-tert-Butyl-3-methoxy-phenylamine
CAS Number:35291-89-5
Molecular formula:C11H17NO
Molecular Weight:179.26

1H-Isoindole-1,3(2H)-dione, 2-[4-(1,1-dimethylethyl)-3-methoxyphenyl]-

1233531-37-7
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35291-89-5
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Yield:35291-89-5 82%

Reaction Conditions:

with hydrazine in ethanol; for 3 h;Reflux;

Steps:

24

A slurry of 2-(4-tert-butyl-3-methoxy-phenyl)isoindoline-1,3-dione (400 mg, 1.29 mmol) and NH₂NH₂ (207 mg, 203 μL, 6.47 mmol) in ethanol (10 mL) was refluxed for 3 h. The reaction was cooled and concentrated in vacuo. The residue was extracted with water (25 mL) and ethyl acetate (3*10 mL). The combined organic extracts were washed with water, dried over Na₂SO₄, filtered and concentrated. Purification by silica gel chromatography (25-40% ethyl acetate/hexanes) provided 4-tert-butyl-3-methoxy-aniline (190 mg, 82% yield) as light brown oil. ¹H NMR (400.0 MHz, CDCl₃) δ 6.97 (d, J=8.1 Hz, 1H), 6.17 (m, 2H), 3.71 (d, J=3.3 Hz, 3H), 3.53 (br s, 2H), 1.25 (d, J=3.3 Hz, 9H)

References:

US2010/168094,2010,A1 Location in patent:Page/Page column 65