Methanol → Methyl 4-amino-2,5-dimethylbenzoate

To a stirred solution of methyl 2,5-dimethyl-4-nitrobenzoate (523 mg, 2.5 mmol) in a 9:1 mixture of methanol and water (25 mL total) at 0° C. was added ammonium chloride (401 mg, 7.5 mmol). Zinc (1.63 g, 25 mmol) was added portionwise and the resulting mixture was stirred at room temperature overnight. The reaction mixture was then filtered through Celite and the Celite pad was washed with methanol. The filtrate was concentrated under reduced pressure and the resulting residue was dissolved in ethyl acetate. This solution was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide methyl 4-amino-2,5-dimethylbenzoate (450 mg) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.14 (s, 3H), 2.53 (s, 3H), 3.83 (s, 3H), 3.85 (br s, 2H), 6.48 (s, 1H), 7.72 (s, 1H).

1. filtrationThe reaction mixture was then filtered through Celite
2. washthe Celite pad was washed with methanol
3. concentrationThe filtrate was concentrated under reduced pressure
4. dissolutionthe resulting residue was dissolved in ethyl acetate
5. washThis solution was washed with saturated aqueous sodium bicarbonate
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-56677d9e47984b6cbd4d15fa28c1edd7

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524965B2