3'-Bromoacetophenone → HCID 16789189, compound

HRID 1912447Notes

Reaction equation

HRID 1912447 reaction equation
C[Si]([C:5]#[N:6])(C)C.[CH3:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)=O.[NH4+:17].[Cl-]>N.CO>[NH2:17][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=1)([CH3:7])[C:5]#[N:6]

Participants

5

Reactant 3

HCID 165023'-BromoacetophenoneHCID 25517Ammonium ChlorideHCID 82115Trimethylsilyl cyanide

Product 1

HCID 16789189HCID 16789189, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Trimethylsilylcyanide (20 g, 200 mmol) was added to a stirred solution of 3-bromoacetophenone (20 g, 100 mmol) and NH4Cl (11 g, 200 mmol) in NH3/MeOH (400 mL). The mixture was stirred at room temperature for 4 days. Then the solvent was evaporated in vacuo and the residue was taken up in AcOEt (100 mL). The solid was filtered off and the filtrate was evaporated in vacuo to yield rac-2-amino-2-(3-bromo-phenyl)-propionitrile (20 g, 86% yield) which was used in the next step without further purification.

Workup

  1. customThen the solvent was evaporated in vacuo
  2. filtrationThe solid was filtered off
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-dfeb6b396daa454984ee3da84f87b297
Source dataset
uspto-grants-2013_12
Patent number
US08609660B2

Reaction notes

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