Benzylamine → 2-Benzyl-5,6-dimethoxyisoindoline

HRID 1032484Notes

Reaction equation

HRID 1032484 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-dimethoxyisoindoline

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

2.35 g (10 mmol) of 4,5-bis(chloromethyl)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 Starks catalyst (a 90% aqueous solution), and the mixture was stirred for 20 hours. The organic layer was separated, dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The crystal residue was washed with diisopropyl ether to obtain 1.87 g of the above identified compound as colorless needle crystals.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. washThe crystal residue was washed with diisopropyl ether
  5. customto obtain 1.87 g of the

Sources & evidence

ORD record
ord-7aa1bff1cdd44aa3afbfe1da33b6d834
Source dataset
uspto-grants-1990_09
Patent number
US04958029

Reaction notes

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