Triethylsilane → 2-(3-Aminophenoxy)-N-cyclopropylacetamide

HRID 1487107Notes

Reaction equation

HRID 1487107 reaction equation
C([SiH](CC)CC)C.[CH:8]1([NH:11][C:12](=[O:24])[CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH2:10][CH2:9]1>CO.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=1)[O:14][CH2:13][C:12]([NH:11][CH:8]1[CH2:9][CH2:10]1)=[O:24]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 7865440N-cyclopropyl-2-(3-nitrophenoxy)acetamide

Product 1

HCID 167764562-(3-Aminophenoxy)-N-cyclopropylacetamideYield 81.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Triethylsilane (27.0 ml, 169 mmol) was added dropwise to a suspension of N-cyclopropyl-2-(3-nitrophenoxy)acetamide (4 g, 16.93 mmol) and Pd/C (10%, 400 mg) in MeOH (50 ml). Resulting suspension was stirred at RT for 20 min. and filtered through celite. The filtrate was evaporated under vacuum and triturated in hexane to obtain the crystals which were collected by filtration to afford 2-(3-aminophenoxy)-N-cyclopropylacetamide (2.86 gm).

Workup

  1. customResulting suspension
  2. filtrationfiltered through celite
  3. customThe filtrate was evaporated under vacuum
  4. customtriturated in hexane
  5. customto obtain the crystals which
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-f1f59e9fc0f743aab7ae0aa275862ea3
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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