Ammonia → 4'-(Aminomethyl)-biphenyl-3-carboxylic acid

HRID 735846Notes

Reaction equation

HRID 735846 reaction equation
[NH3:1].C([O:6][C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8])(C)(C)C>CO>[C:7]([C:9]1[CH:10]=[C:11]([C:15]2[CH:22]=[CH:21][C:18]([CH2:19][NH2:1])=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([OH:6])=[O:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 183986744-(3-Tert-butoxy carbonyl phenyl)benzyl bromide

Product 1

HCID 223110384'-(Aminomethyl)-biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ammonia gas was passed through a cooled solution of 4-(3-tert-butoxycarbonylphenyl) benzyl bromide (65 g, 0.18 mol) in methanol (2 L) for 6 h. Then the reaction mixture was stirred at RT overnight. Methanol was removed under vacuum. To the residue 6N aqueous solution of HCl (200 mL) was added and stirred overnight. Concentrated completely to get 4-(3-carboxyphenyl)benzylamine as a hydrochloride salt (20 g, 41%).

Workup

  1. customMethanol was removed under vacuum
  2. additionTo the residue 6N aqueous solution of HCl (200 mL) was added
  3. stirringstirred overnight
  4. concentrationConcentrated completely

Sources & evidence

ORD record
ord-4151176dd32046dda93891a3c54c36b4
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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