Ammonium Chloride → 1-(4-Aminophenyl)-2-(tert-butyldimethylsilyloxy)ethanone

HRID 1807251Notes

Reaction equation

HRID 1807251 reaction equation
[Si:1]([O:8][CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)=[O:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.[Zn]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:10](=[O:11])[CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 199641862-(Tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone

Product 1

HCID 592495591-(4-Aminophenyl)-2-(tert-butyldimethylsilyloxy)ethanoneYield 82.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Step B To a solution of 2-(tert-butyldimethylsilyloxy)-1-(4-nitrophenyl)ethanone (0.54 g, 1.83 mmol) in methanol (60 mL) was added an aqueous solution (15 mL) of ammonium chloride (0.98 g, 18.3 mmol), followed by the addition of Zinc (1.2 g, 18.3 mmol). The reaction mixture was stirred at room temperature for 1 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to a small volume, then when partitioned between ethyl acetate and water. The organic layer was separated, the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over MgSO4, and concentrated to give 1-(4-amino-phenyl)-2-(tert-butyl-dimethyl-silanyloxy)-ethanone as a white foam (0.4 g, 82%)

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated to a small volume
  3. customwhen partitioned between ethyl acetate and water
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washwashed with water, brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9a8dc33c17f045efa960916bd0998f01
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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