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

HRID 250464

反応式

HRID 250464 の反応式
C(=O)([O-])[O-].[K+].[K+].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][C:13]2=[O:20])([O-:9])=[O:8].[CH2:21]([O:23][C:24](=[O:27])[CH2:25]Br)[CH3:22]>>[CH2:21]([O:23][C:24](=[O:27])[CH2:25][N:14]1[C:13](=[O:20])[C:12]2[C:16](=[CH:17][CH:18]=[C:10]([N+:7]([O-:9])=[O:8])[CH:11]=2)[C:15]1=[O:19])[CH3:22]

参加物

4

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 611.2%

実験手順

Potassium carbonate (57.8 g) was added to a solution mixture of 5-nitro-isoindole-1,3-dione (26.2 g) and bromo-acetic acid ethyl ester (25.1 g) in actone (500 ml). The resulting mixture was refluxed overnight (18 h). After cooling, reaction mixture was filtered and rinsed with ethyl acetate. Filtrate was concentrated and the residue was triturated with ether (200 ml). Solid was collected and rinsed with ether. Dried in vacuo to give the title compound 231.9 g. 1H NMR (200 MHz, CDCl3) δ 8.69 (m, 2H), 8.07 (d, J=8.2 Hz, 1H), 4.48 (s, 2H), 4.24 (q, J=7.0 Hz, 2H), 1.30 (t, J=7.0 Hz, 3H).

後処理

  1. temperatureThe resulting mixture was refluxed overnight (18 h)
  2. temperatureAfter cooling
  3. customreaction mixture
  4. filtrationwas filtered
  5. washrinsed with ethyl acetate
  6. concentrationFiltrate was concentrated
  7. customthe residue was triturated with ether (200 ml)
  8. customSolid was collected
  9. washrinsed with ether
  10. customDried in vacuo

出典と根拠

ORDレコード
ord-1c30918a772144c6888f44cb5fd3da84
出典データセット
uspto-grants-2011_01
特許番号
US07863292B2

関連ノート

読み込み中…