Water → 4-Benzyloxybenzylamine

HRID 2080034Notes

Reaction equation

HRID 2080034 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN.O>C(O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][NH2:14])=[CH:25][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 23130715HCID 23130715, compound

Product 1

HCID 42928454-Benzyloxybenzylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Next, to a solution of the resulting 2-(4benzyloxybenzyl)-isoindol-1,3-dione (37 g, 0.107 mol) in ethanol (1 L) was added hydrazine monohydrate (8.04 g, 0.161 mol), and the solution was stirred for 8 hours under reflux. The reaction solution was allowed to room temperature, then, water was added, and ethanol was evaporated in vacuo. Ethyl acetate and water were added to the residue for partitioning, the organic layer was washed with water, an aqueous solution of 2N sodium hydroxide and water, in this order, and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=2:1; hereinafter, the NH silica gel used was manufactured by Fuji Silysia), and the title compound (15 g, 64%) was obtained as a white solid.

Workup

  1. temperatureunder reflux
  2. customwas allowed to room temperature
  3. customethanol was evaporated in vacuo
  4. additionEthyl acetate and water were added to the residue
  5. customfor partitioning
  6. washthe organic layer was washed with water
  7. dry with materialan aqueous solution of 2N sodium hydroxide and water, in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated
  9. customthe residue was purified by NH silica gel column chromatography (hexane
  10. customwas obtained as a white solid

Sources & evidence

ORD record
ord-5f87863e1ae44bdb9332d4ba47c4f35e
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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