O-Methylhydroxylamine → 3-Amino-4-nitropyridine

HRID 265634

反応式

HRID 265634 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 5869433-Amino-4-nitropyridine収率 25.2%

試薬・触媒・溶媒 3

HCID 3007855Zincchloride触媒HCID 6228Dimethylformamide溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f352db06847e43c7b3aa6d376b97850d
出典データセット
uspto-grants-1997_07
特許番号
US05648496

関連ノート

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