Sodium Hydroxide → (3-(Benzyloxy)phenyl)hydrazine hydrochloride

HRID 522160노트

반응식

HRID 522160 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]([O-])=O.[Na+].[Sn](Cl)[Cl:21].[OH-].[Na+]>O.Cl>[ClH:21].[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:12][NH2:16])[CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 928923-BenzyloxyanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 12891839(3-(Benzyloxy)phenyl)hydrazine hydrochloride수율 83%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매2회HCID 962Water용매

실험 절차

3-(benzyloxy)aniline (5 g, 25.09 mmol) was added dropwise to 6M HCl (100 mL) at 4° C. A solution of sodium nitrite (3.46 g, 50.19 mmol) in water (50 mL) was added dropwise over 10 minutes and the reaction was stirred for 1 hour. A solution of tin (II) chloride (17.53 g, 77.7 mmol) in 6M HCl (150 mL) was added dropwise over 20 minutes, maintaining the internal temperature below 7° C. The suspension was stirred for 2 hours before neutralising then basifying the reaction to pH>12 using sodium hydroxide. The aqueous layer was extracted with diethyl ether (3×150 mL), the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The yellow oil was dissolved in HCl in methanol and concentrated in vacuo. The resulting solid was triturated with diethylether, filtered and dried in vacuo to afford the title compound as purple solid (5.22 g, 83%).

후처리

  1. temperaturemaintaining the internal temperature below 7° C
  2. stirringThe suspension was stirred for 2 hours
  3. customthe reaction to pH>12
  4. extractionThe aqueous layer was extracted with diethyl ether (3×150 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe yellow oil was dissolved in HCl in methanol
  8. concentrationconcentrated in vacuo
  9. customThe resulting solid was triturated with diethylether
  10. filtrationfiltered
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-1ca4e2de60964b61975bbad9bde04a9a
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328096B2

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