تفاعل #78747

معادلة التفاعل

3-(methoxymethyl)nitrobenzene

3-(methoxymethyl)nitrobenzene

→

3-(methoxymethyl)aniline

المردود 99.1%

المذيبات

acetic acid

ظروف التفاعل

المعالجة

1. 1
   ترشيحThe reaction mixture was filtered through celite and
2. 2
   تركيزconcentrated in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
4. 4
   غسيلwashed with aqueous saturated sodium bicarbonate
5. 5
   غسيلThe organic layer was washed with water
6. 6
   تجفيفdried over MgSO4
7. 7
   تركيزconcentrated in vacuo

الإجراء التجريبي

EX-514B) The 3-(methoxymethyl)nitrobenzene (4.18 g, 25 mmol) from EX-514A was dissolved in 160 mL of acetic acid. Zinc dust (5 g, 76.5 mmol) was added, and the solution was stirred at room temperature for 18 hours, at which time HPLC analysis indicated that no 3-(methoxymethyl)nitrobenzene starting material remained. The reaction mixture was filtered through celite and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with aqueous saturated sodium bicarbonate. The organic layer was washed with water, then dried over MgSO4, and concentrated in vacuo to give 3.4 g (99%) of the desired 3-(methoxymethyl)aniline as a brown oil. The crude product was used without further purification. HRMS calcd. for C8H12NO: 138.0919 [M+H]+, found: 138.0929. 1H NMR (CDCl3) δ 3.4 (s, 3H), 3.7 (s, 2H), 4.4 (s, 2H), 6.6 (d, 1H), 6.7 (m, 2H), 7.2 (t, 1H).

المصدر