Acetic Acid → 1-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one

HRID 62437

反応式

HRID 62437 の反応式
C[N:2]([CH:4]=[C:5]1[C:10](=[O:11])[CH2:9][CH2:8][CH2:7][C:6]1=O)C.[CH3:13][NH:14]N.CC(O)=O>CC(O)(C)C>[CH3:13][N:14]1[C:6]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:5]=2[CH:4]=[N:2]1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 6061MethylhydrazineHCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dione

生成物 1

HCID 27657961-Methyl-1,5,6,7-tetrahydro-4H-indazol-4-one収率 44.4%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

To a solution of 2-((dimethylamino)methylene)cyclohexane-1,3-dione (55 g crude, 300 mmol) in t-BuOH (400 ml) was added methylhydrazine solution (35 g, 40% aqueous solution, 304 mmol) and AcOH (20 ml) at room temperature. The resulting mixture was heated to reflux for 3 h under nitrogen protection. After cooling, the mixture was concentrated in vacuo and the residue was purified by column chromatograph on silica gel (petroleum ether/ethyl acetate=1/1 v/v %) to give 1-methyl-6,7-dihydro-1H-indazol-4(5H)-one (20 g, two steps: 44%). MS-ESI (m/z): 151 (M+1)+ (Acq Method: 0-60AB_2 min; Rt: 0.90 min)

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h under nitrogen protection
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. customthe residue was purified by column chromatograph on silica gel (petroleum ether/ethyl acetate=1/1 v/v %)

出典と根拠

ORDレコード
ord-c91a85ec21ff40dc99f2dd9f138c943d
出典データセット
uspto-grants-2016_09
特許番号
US09446130B2

関連ノート

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