反応 #4477

反応方程式

4-benzyloxyaniline hydrochloride

sodium nitrite

→

[4-(Phenylmethoxy)phenyl]hydrazine hydrochloride

溶媒

hydrochloric acid

water

反応条件

後処理

1. 1
   workup.ADDITIONThe temperature was kept between -6° and -12° during the addition
2. 2
   workup.STIRRINGstirring
3. 3
   ろ過The mixture was filtered (Hyflo)
4. 4
   温度the filtrate cooled to ca -18°
5. 5
   workup.ADDITIONThe solution of the diazonium salt was then added to a cold (-12°)
6. 6
   workup.STIRRINGstirred solution of tin (II) chloride dihydrate (157.9 g) in concentrated hydrochloric acid (400 ml) over a period of ca 0.5 h
7. 7
   workup.ADDITIONDuring the addition the temperature
8. 8
   その他gradually rose to 0°
9. 9
   workup.STIRRINGsubsequently stirring
10. 10
    workup.WAITwas continued for 2 h
11. 11
    その他to reach room temperature
12. 12
    ろ過Filtration of the suspension
13. 13
    その他afforded a solid
14. 14
    洗浄This material was washed with anhydrous ether (750 ml)
15. 15
    その他dried at room temperature for ca 16 h

実験手順

A solution of sodium nitrite (16.1 g) in water was added dropwise over a period of ca 0.75 h to a cold (salt-ice bath) stirred suspension of 4-benzyloxyaniline hydrochloride (50 g) in concentrated hydrochloric acid (120 ml). The temperature was kept between -6° and -12° during the addition and stirring was continued for 1 h at the same temperature. The mixture was filtered (Hyflo) and the filtrate cooled to ca -18°. The solution of the diazonium salt was then added to a cold (-12°) stirred solution of tin (II) chloride dihydrate (157.9 g) in concentrated hydrochloric acid (400 ml) over a period of ca 0.5 h. During the addition the temperature gradually rose to 0°, and subsequently stirring was continued for 2 h while allowing the reaction mixture to reach room temperature. Filtration of the suspension afforded a solid. This material was washed with anhydrous ether (750 ml) and dried at room temperature for ca 16 h to present the title compound as a powder (34.4 g) m.p. 165°-170°. T.l.c. (E), Rf 0.5.

出典