Toluene → 4-[2-(2,3-Dihydro-5,6-dimethoxy-1H-isoindol-2-yl)ethyl]benzenamine

HRID 1451649

반응식

HRID 1451649 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([O:13][CH3:14])[C:6]([O:11][CH3:12])=[CH:7][C:8]=1[CH2:9]Cl.[OH-].[Na+].C1(C)C=CC=CC=1.[NH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][NH2:33])=[CH:27][CH:26]=1>O>[CH3:14][O:13][C:5]1[CH:4]=[C:3]2[C:8](=[CH:7][C:6]=1[O:11][CH3:12])[CH2:9][N:33]([CH2:32][CH2:31][C:28]1[CH:29]=[CH:30][C:25]([NH2:24])=[CH:26][CH:27]=1)[CH2:2]2

참가 물질

6

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 728952-(4-Aminophenyl)ethylamineHCID 109444001,2-Bis(chloromethyl)-4,5-dimethoxybenzene

생성물 1

HCID 199745564-[2-(2,3-Dihydro-5,6-dimethoxy-1H-isoindol-2-yl)ethyl]benzenamine

시약·촉매·용매 1

HCID 962Water용매

실험 절차

4,5-Bischloromethyl veratrol (2.35 g: S. H. Wood, M. A. Peny and C. C. Tung, J. A. C. S. (1950), 72, 2989-2991) was added at room temperature to a stirred suspension of 50% aqueous sodium hydroxide (5 ml), toluene (25 ml), 4-aminophenylethylamine (1.5 g) and Aliquat (0.2 g). The heterogeneous mixture was stirred at room temperature for 16 hours, poured in water and extracted with methylene chloride. The organic layer was dried and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with methylene dichloride/methanol (95:5) to give the title compound as a solid (0.6 g), MP: 150°. NMR includes signals at d 2.7(4H,m,Ph--CH2 --CH2 --N); 4.6(2H,bs,NH2); 3.7(6H,s,2×OCH3); 3.8(4H,s,2×N--CH2Ph); 6.2-7.0(6H,m,aromatics).

후처리

  1. extractionextracted with methylene chloride
  2. customThe organic layer was dried
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with methylene dichloride/methanol (95:5)

출처 및 근거

ORD 기록
ord-bc39019733d845728ef69ee9952ea420
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05604237

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