O-Methylhydroxylamine → 2-Amino-6-methoxy-3-nitropyridine

HRID 265633

반응식

HRID 265633 반응식
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.CO[NH2:14].CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O.[Cl-].[Zn+2].[Cl-]>[NH2:14][C:7]1[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

참가 물질

7

반응물 4

HCID 4113O-MethylhydroxylamineHCID 25517Ammonium ChlorideHCID 795252-Methoxy-5-nitropyridineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 38524282-Amino-6-methoxy-3-nitropyridine수율 87%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
25 °C

실험 절차

6-Methoxy-3-nitropyridine (154 mg, 1 mmol) and O-methylhydroxylamine (71 mg, 1.5 mmol) were dissolved in DMSO (2 ml), and a resulting solution was added dropwise to a DMSO 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 stirred at 25 ° C. for 9 hours 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 subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1] to obtain 147 mg of 2-amino-6-methoxy-3-nitropyridine (yield: 87%).

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 by subjection to silica gel thin layer chromatography [eluent: ethyl acetate/hexane=1/1]

출처 및 근거

ORD 기록
ord-e2e437f90535462b87ba39f110724f13
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648496

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