反应详情

2-(3-Nitro-4-hydroxyphenyl) propionitrile (123.8 g., 0.64 mole.) was suspended in absolute ethanol (950 ml.) and added during 20 minutes, with cooling, to a solution of stannous chloride dihydrate (437.8 g., 1.94 mole.) in concentrated hydrochloride acid (591 ml., 7 mole.). The addition was made at such a rate that the temperature of the reaction mixture did not exceed 20°C. Stirring of the mixture was continued for a further 19 hours at room temperature. The resulting solution, together with ice (1.75 kg.) was added during one hour to a cooled solution of sodium hydroxide (650 g.) in water (600 ml.). The temperature of the reaction mixture was maintained at 15° - 20°C during the addition. The mixture was stirred for a further 1 hour, and the pH then adjusted to 6 by the addition of concentrated hydrochloric acid. The resulting suspension was filtered and the filtrate saturated with sodium chloride, then extracted with ether (×6). The combined ether extracts were dried (Na2SO4) and evaporated to leave a solid (69.15 g.) which was suspended in chloroform and extracted with 2N-hydrochloric acid (×6). The combined acid extracts were neutralised to pH 7-8 by the addition of sodiium bicarbonate. The resulting suspension was extracted with ether (×4). The combined ether extracts were washed twice with water, dried (Na2SO4), and evaporated to yield 2-(3-amino-4-hydroxyphenyl) propionitrile was a light brown solid (62.85 g.), m.p. 110° - 112°C.

1. additionadded during 20 minutes
2. additionThe addition
3. customdid not exceed 20°C
4. temperatureThe temperature of the reaction mixture was maintained at 15° - 20°C during the addition
5. stirringThe mixture was stirred for a further 1 hour
6. filtrationThe resulting suspension was filtered
7. extractionthe filtrate saturated with sodium chloride, then extracted with ether (×6)
8. dry with materialThe combined ether extracts were dried (Na2SO4)
9. customevaporated
10. customto leave a solid (69.15 g.) which
11. extractionextracted with 2N-hydrochloric acid (×6)
12. additionThe combined acid extracts were neutralised to pH 7-8 by the addition of sodiium bicarbonate
13. extractionThe resulting suspension was extracted with ether (×4)
14. washThe combined ether extracts were washed twice with water
15. dry with materialdried (Na2SO4)
16. customevaporated