4-Benzyloxyaniline hydrochloride → (4-(Benzyloxy)phenyl)hydrazine monohydrochloride

HRID 4381

반응식

HRID 4381 반응식
[N:1]([O-])=O.[Na+].[ClH:5].[CH2:6]([O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O.Cl>[ClH:5].[C:7]1([CH2:6][O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:18][NH2:1])=[CH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 27238314-Benzyloxyaniline hydrochlorideHCID 23668193Sodium Nitrite

생성물 1

HCID 3016725(4-(Benzyloxy)phenyl)hydrazine monohydrochloride

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 962Water용매

실험 절차

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.

후처리

  1. additionThe temperature was kept between -6° and -12° during the addition
  2. stirringstirring
  3. filtrationThe mixture was filtered (Hyflo)
  4. temperaturethe filtrate cooled to ca -18°
  5. additionThe solution of the diazonium salt was then added to a cold (-12°)
  6. 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. additionDuring the addition the temperature
  8. customgradually rose to 0°
  9. stirringsubsequently stirring
  10. waitwas continued for 2 h
  11. customto reach room temperature
  12. filtrationFiltration of the suspension
  13. customafforded a solid
  14. washThis material was washed with anhydrous ether (750 ml)
  15. customdried at room temperature for ca 16 h

출처 및 근거

ORD 기록
ord-63297f81bc0d4054a9441052d946e9fe
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725615

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