Triethylsilane → 2-(3-Aminophenyl)-2-methylpropanamide

HRID 1487113Notes

Reaction equation

HRID 1487113 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)([CH3:6])[C:3]([NH2:5])=[O:4].C([SiH](CC)CC)C>CO.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([C:2]([CH3:6])([CH3:1])[C:3]([NH2:5])=[O:4])[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 671059682-Methyl-2-(3-nitrophenyl)propanamide

Product 1

HCID 898152702-(3-Aminophenyl)-2-methylpropanamideYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 2-methyl-2-(3-nitrophenyl)propanamide (0.9 g, 4.32 mmol) in methanol was added Pd—C (10%, 0.23 g) followed by slow addition of triethylsilane (6.90 ml, 43.2 mmol) at RT. Reaction was stirred at same temperature for 25 min. The reaction mixture was filtered through celite bed and washed with methanol (50 ml). Filtrate was collected and concentrated under vacuum to obtain 2-(3-aminophenyl)-2-methylpropanamide (0.611 g).

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered through celite bed
  3. washwashed with methanol (50 ml)
  4. customFiltrate was collected
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1b4eae77f21742e194fc76a44504305a
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

Loading…