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

HRID 1451649

反応式

HRID 1451649 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bc39019733d845728ef69ee9952ea420
出典データセット
uspto-grants-1997_02
特許番号
US05604237

関連ノート

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