Methylhydrazine → 6-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750126ノート

反応式

HRID 750126 の反応式
[CH3:1][O:2][C:3]([C:5]1[O:6][C:7]([C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=O)=[O:4].[CH3:23][NH:24][NH2:25]>CO>[CH3:1][O:2][C:3]([C:5]1[N:25]([NH:24][CH3:23])[C:7](=[O:6])[C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:4]

参加物

4

反応物 2

HCID 6061MethylhydrazineHCID 691565656-chloro-4-phenylisocoumarin-3-carboxylic Acid Methyl Ester

生成物 1

HCID 101259456-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester収率 69.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 6-chloro-4-phenylisocoumarin-3-carboxylic acid methyl ester (1.3 g) in methanol (15 ml) was added methylhydrazine (3.0 g) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the obtained residue was dissolved in methanol (15 ml). Sulfuric acid (1.5 ml) was added and the mixture was refluxed for 2 hrs. The reaction mixture was concentrated, and the residue was neutralized with aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) and crystallized from isopropyl ether to give the title compound (980 mg) as colorless crystals.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe obtained residue was dissolved in methanol (15 ml)
  3. additionSulfuric acid (1.5 ml) was added
  4. temperaturethe mixture was refluxed for 2 hrs
  5. concentrationThe reaction mixture was concentrated
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
  11. customcrystallized from isopropyl ether

出典と根拠

ORDレコード
ord-941595252bc04a11b72c7d49a9ad390a
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

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