Sodium Hydroxide → 4-[N-(5-Bromo-2-(phenethyl)benzyl)amino]Benzoic Acid

HRID 1006000Notes

Reaction equation

HRID 1006000 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:6]([CH:19]=1)[CH2:7][NH:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[C:6]([CH:19]=1)[CH2:7][NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675570Methyl 4-[N-(5-bromo-2-(phenethyl)benzyl)amino]benzoate

Product 1

HCID 226755474-[N-(5-Bromo-2-(phenethyl)benzyl)amino]Benzoic AcidYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 4-[N-(5-bromo-2-(phenethyl)benzyl)amino]benzoate (0.25 g) and 2N aqueous NaOH (5 ml) were heated at reflux in a mixture of methanol (5 ml) and THF (5 ml) for 2 hours. The organic solvents were evaporated, the residue acidified with 2N HCl and extracted with ethyl acetate. The extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by crystallisation from diethyl ether and hexane to give the title compound (0.23 g; mpt 132-134° C.).

Workup

  1. customThe organic solvents were evaporated
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by crystallisation from diethyl ether and hexane

Sources & evidence

ORD record
ord-bce797bfc3054367a2e4ef38d46186d3
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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