Sodium Hydroxide → 4-[N-(2-Benzyloxy-5-bromobenzyl)aminomethyl]Benzoic Acid

HRID 355753Notes

Reaction equation

HRID 355753 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][NH:12][CH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([O:20]CC)=[O:19])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][C:10]=1[CH2:11][NH:12][CH2:13][C:14]1[CH:24]=[CH:23][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22675503ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

Product 1

HCID 47205174-[N-(2-Benzyloxy-5-bromobenzyl)aminomethyl]Benzoic AcidYield 60.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)-aminomethyl]benzoate (1.4 g) in methanol (25 ml) was added 2N sodium hydroxide solution (7.7 ml). The mixture was heated at reflux for 30 minutes, left to stand for 2 hours at ambient temperature, the solvent evaporated and the residue mixed with water (20 ml). The mixture was acidified with acetic acid, the precipitate filtered off and crystallised form ethyl acetate to give the title compound (800 mg) mpt 209° C. The starting material was prepared as follows:

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 minutes
  3. waitleft
  4. customthe solvent evaporated
  5. additionthe residue mixed with water (20 ml)
  6. filtrationthe precipitate filtered off
  7. customcrystallised
  8. customform ethyl acetate

Sources & evidence

ORD record
ord-54ac1ecaf32544c38fb271baa258bb44
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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