4-Nitrophthalimide → (5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester

HRID 409292

反応式

HRID 409292 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[NH:10][C:8](=[O:9])[C:7]2=[CH:13][CH:14]=1)([O-:3])=[O:2].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][N:10]1[C:11](=[O:12])[C:6]2[C:7](=[CH:13][CH:14]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:8]1=[O:9])[CH3:21]

参加物

5

反応物 3

HCID 69694-NitrophthalimideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

生成物 1

HCID 784823(5-Nitro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetic acid ethyl ester収率 89.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of 4-nitrophthalimide (82.54 g, 0.43 mol), ethyl bromoacetate (78.92 g, 0.47 mol) and potassium carbonate (130.6 g, 0.94 mol), and acetone (1.5 l) was refluxed for eighteen hours before it was cooled to room temperature, filtered and concentrated in vacuo. The residue was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a yellow solid (107.39 g): MS: (+) m/z 279.25 (M+1).

後処理

  1. temperaturewas refluxed for eighteen hours before it
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between dichloromethane and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7bff02a827b248418e5164c7a19d1b7f
出典データセット
uspto-grants-2014_06
特許番号
US08759373B2

関連ノート

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