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

HRID 1005996Notes

Reaction equation

HRID 1005996 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.

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-9b9cfa63525041f2a39fb741bcedd64a
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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