Acetic Anhydride → 1-acetyl-6-methyl-1H-indazol-5-yl acetate

HRID 1269822ノート

反応式

HRID 1269822 の反応式
C(OC(=O)C)(=O)C.C([O-])(=O)C.[K+].[N:13](OCCC(C)C)=O.[C:21]([O:24][C:25]1[CH:30]=[C:29]([CH3:31])[C:28]([NH:32][C:33](=[O:35])[CH3:34])=[CH:27][C:26]=1[CH3:36])(=[O:23])[CH3:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>[C:21]([O:24][C:25]1[CH:30]=[C:29]2[C:28](=[CH:27][C:26]=1[CH3:36])[N:32]([C:33](=[O:35])[CH3:34])[N:13]=[CH:31]2)(=[O:23])[CH3:22]

参加物

8

反応物 4

HCID 7918Acetic AnhydrideHCID 8053Isoamyl NitriteHCID 517044Potassium AcetateHCID 190786134-(Acetylamino)-2,5-dimethylphenyl acetate

生成物 1

HCID 694307581-acetyl-6-methyl-1H-indazol-5-yl acetate収率 46%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetic anhydride (0.96 ml, 10.2 mmol), tetrabutylammonium bromide (55 mg, 0.169 mmol), potassium acetate (665 mg, 6.78 mmol) and isoamyl nitrite (0.592 ml, 4.41 mmol) were added to a solution of 4-(acetylamino)-2,5-dimethylphenyl acetate (750 mg, 3.39 mmol) in ethyl acetate (7.5 ml) at room temperature, and the resulting mixture was refluxed. After 9 hours, the reaction solution was poured into water (50 ml) and extracted with ethyl acetate (50 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain 1-acetyl-6-methyl-1H-indazol-5-yl acetate (359 mg, 46%).

後処理

  1. temperaturethe resulting mixture was refluxed
  2. extractionextracted with ethyl acetate (50 ml×2)
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customThe organic layer dried
  5. concentrationwas concentrated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-3617566acb644d40b8982d67857f84d5
出典データセット
uspto-grants-2007_04
特許番号
US07199147B2

反応ノート

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