Triethylsilane → HCID 28689687, compound

HRID 1487105Notes

Reaction equation

HRID 1487105 reaction equation
[CH:1]1([NH:4][C:5](=[O:16])[CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=2)[CH2:3][CH2:2]1.C([SiH](CC)CC)C>CO.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([CH2:6][C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[O:16])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 89814640HCID 89814640, compound

Product 1

HCID 28689687HCID 28689687, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of N-cyclopropyl-2-(3-nitrophenyl)acetamide (2.4 g, 10.90 mmol) in methanol (25.0 ml) was added slurry of Pd/C (10%, 0.232 g), To the above reaction mixture, triethylsilane (8.70 ml, 54.5 mmol) was added slowly drop wise at room temperature (reaction was exothermic) and then the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was filtered through celite bed and the filtrate was evaporated under vacuum. The residue was triturated in hexane, the solid obtained was filtered and dried under vacuum to give the product (1.95 gm).

Workup

  1. custom(reaction was exothermic)
  2. filtrationThe reaction mixture was filtered through celite bed
  3. customthe filtrate was evaporated under vacuum
  4. customThe residue was triturated in hexane
  5. customthe solid obtained
  6. filtrationwas filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-96df5b4684924809ab0451f59d65dc7c
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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