Hydrogen Bromide → N-benzyl-5,6-dihydroxy-N-methylisoindolinium bromide

HRID 1032482Notes

Reaction equation

HRID 1032482 reaction equation
[I-].[CH2:2]([N+:9]1([CH3:22])[CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:20]C)=[C:14]([O:18]C)[CH:15]=2)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BrH:23]>>[Br-:23].[CH2:2]([N+:9]1([CH3:22])[CH2:10][C:11]2[C:16](=[CH:15][C:14]([OH:18])=[C:13]([OH:20])[CH:12]=2)[CH2:17]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 14993733HCID 14993733, compound

Product 1

HCID 14993734N-benzyl-5,6-dihydroxy-N-methylisoindolinium bromide

Conditions

Temperature
120 °C

Procedure

To 10 g (24.3 mmol) of N-benzyl-5,6-dimethoxy-N-methylisoindolinium iodide, 50 ml of 48% hydrobromic acid was added, and the mixture was heated at reflux for 3 hours at an external temperature of 120° C. The reaction solution was evaporated to dryness under reduced pressure, and the crystal residue was washed with 20 ml of acetone to obtain 6.90 g of the above identified compound. The filtrate was left to stand overnight, to obtain 190 mg of the secondary crystals. The total yield was 7.09 g. The melting point, the infrared absorption spectrum and the 1H-NMR spectrum of this product agreed to those of Example 2.

Workup

  1. temperaturethe mixture was heated
  2. customThe reaction solution was evaporated to dryness under reduced pressure
  3. washthe crystal residue was washed with 20 ml of acetone
  4. customto obtain 6.90 g of the
  5. waitThe filtrate was left

Sources & evidence

ORD record
ord-0b6469ff780e4eb2af4f2afb16b8129d
Source dataset
uspto-grants-1990_09
Patent number
US04958029

Reaction notes

Loading…