Benzylamine → 2-Benzyl-5,6-dimethoxyisoindoline

HRID 704453Notes

Reaction equation

HRID 704453 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+].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1(C)C=CC=CC=1>[CH2:17]([N:24]1[CH2:9][C:8]2[C:3](=[CH:4][C:5]([O:13][CH3:14])=[C:6]([O:11][CH3:12])[CH:7]=2)[CH2:2]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 109444001,2-Bis(chloromethyl)-4,5-dimethoxybenzene

Product 1

HCID 149937372-Benzyl-5,6-dimethoxyisoindolineYield 70%

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

2.35 g (10 mmol) of 4,5-bischloromethyl veratrol was added at room temperature to a suspension comprising 5 ml of a 50% sodium hydroxide aqueous solution, 25 ml of toluene, 1.25 g (11.66 mmol) of benzylamine and 0.2 g of a Starks catalyst. The mixture was stirred at room temperature for 20 hours, and then the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the crystalline residue was washed with isopropyl ether to obtain 1.87 g (yield: 70.0%) of the above identified compound as colorless needle-like crystals.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. washthe crystalline residue was washed with isopropyl ether
  5. customto obtain 1.87 g (yield: 70.0%) of the

Sources & evidence

ORD record
ord-d67d04b5e2db4dd18e84977f4dd54138
Source dataset
uspto-grants-1991_01
Patent number
US04987235

Reaction notes

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