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

HRID 1451649Notes

Reaction equation

HRID 1451649 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-bc39019733d845728ef69ee9952ea420
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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