O-Methylhydroxylamine → 3-Amino-4-nitropyridine

HRID 265634

반응식

HRID 265634 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].CO[NH2:12].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.[Cl-].[Zn+2].[Cl-].C(OCC)(=O)C.CCCCCC>[NH2:12][C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 4113O-MethylhydroxylamineHCID 25517Ammonium ChlorideHCID 707344-NitropyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 5869433-Amino-4-nitropyridine수율 25.2%

시약·촉매·용매 3

HCID 3007855Zincchloride촉매HCID 6228Dimethylformamide용매2회HCID 21226206Ethyl acetate hexane용매

실험 절차

4-Nitropyridine (124 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMF (2 ml), and a resulting solution was added dropwise to a DMF solution (3 ml) containing potassium tert-butoxide (336 mg, 3 mmol) and zinc (II) chloride (136 mg, 1 mmol) at 25° C. After completion of the addition, the resulting mixture was at 25° C. for one hour and an aqueous saturated ammonium chloride solution (50 ml) was added, followed by extraction with ethyl acetate (80 ml). A resulting organic layer was dried over anhydrous magnesium sulfate, and then isolated and purified by subjecting to silica gel thin layer chromatography (eluent: ethyl acetate/hexane=1/1] to obtain 35 mg of 3-amino-4-nitropyridine (yield: 25%).

후처리

  1. additionAfter completion of the addition
  2. extractionfollowed by extraction with ethyl acetate (80 ml)
  3. dry with materialA resulting organic layer was dried over anhydrous magnesium sulfate
  4. customisolated
  5. custompurified

출처 및 근거

ORD 기록
ord-f352db06847e43c7b3aa6d376b97850d
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648496

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