Water → Methyl 2-amino-2-(3-bromophenyl)propanoate

HRID 1912448Notes

Reaction equation

HRID 1912448 reaction equation
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)([CH3:5])[C:3]#N.C[CH2:14][O:15]C(C)=O.[OH2:19]>Cl.CO>[CH3:14][O:15][C:3](=[O:19])[C:2]([NH2:1])([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[CH:7]=1)[CH3:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 16789189HCID 16789189, compound

Product 1

HCID 50989094Methyl 2-amino-2-(3-bromophenyl)propanoateYield 46%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

rac-2-Amino-2-(3-bromo-phenyl)-propionitrile (20 g, 88.9 mmol) was dissolved in HCl/MeOH (500 mL) and the mixture was refluxed for 4 days. After cooling to room temperature, AcOEt (100 mL) and water (100 mL) were added and the mixture was extracted with AcOEt (2×100 mL). The combined aqueous layers were basified with aqueous ammonia solution until pH 8 and extracted with AcOEt (5×100 mL). The combined organic layers were dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield rac-2-amino-2-(3-bromo-phenyl)-propionic acid methyl ester (10.6 g, 46% yield) as an oil.

Workup

  1. temperaturethe mixture was refluxed for 4 days
  2. extractionthe mixture was extracted with AcOEt (2×100 mL)
  3. extractionextracted with AcOEt (5×100 mL)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents evaporated in vacuo

Sources & evidence

ORD record
ord-f06c41b64a6541549978298ccbe89ee8
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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