Potassium Hydroxide → 5-Hydrazinyl-2-methoxypyridine

HRID 431540

반응식

HRID 431540 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[N:10]([O-])=O.[Na+].O.O.[Sn](Cl)Cl.[OH-].[K+]>Cl.O.C(OCC)C>[NH:1]([C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1)[NH2:10]

참가 물질

8

반응물 4

HCID 14797Potassium HydroxideHCID 61436Stannous chloride dihydrateHCID 811216-Methoxy-3-pyridinylamineHCID 23668193Sodium Nitrite

생성물 1

HCID 222178535-Hydrazinyl-2-methoxypyridine수율 91.6%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매2회HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

5-Amino-2-methoxypyridine (5.0 g, 40 mmol) was dissolved in 6 N HCl (10 mL), cooled to 0° C., and vigorously stirred throughout the procedure. Sodium nitrite (2.8 g, 41 mmol) was dissolved in water (10 mL) and this solution was added to the reaction solution. After 30 min, tin (II) chloride dihydrate (52 g, 230 mmol) in 6 N HCl (20 mL) was added, and the reaction slurry was stirred at 0° C. for 2.5 h. The pH was adjusted to 13 with 40% aqueous potassium hydroxide solution. Ethyl ether was added and the mixture was extracted with EtOAc (4×70 mL), dried (MgSO4) and concentrated to give 5-hydrazino-2-methoxypyridine as an orange solid (5.1 g).

후처리

  1. additionthis solution was added to the reaction solution
  2. stirringthe reaction slurry was stirred at 0° C. for 2.5 h
  3. extractionthe mixture was extracted with EtOAc (4×70 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1eba747551e84b82be1000b2d968109d
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660732B2

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