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

HRID 409292

반응식

HRID 409292 반응식
[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]

참가 물질

5

반응물 3

HCID 69694-NitrophthalimideHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7bff02a827b248418e5164c7a19d1b7f
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

연결된 노트

불러오는 중…