Triethylamine → N-[2-(3-aminophenyl)-1,1-dimethyl-ethyl]-acetamide

HRID 1858322Notes

Reaction equation

HRID 1858322 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])=[CH:4][C:3]=1[N+:16]([O-])=O.C(N(CC)CC)C>C(O)C.[Pd]>[NH2:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])([CH3:11])[CH3:10])[CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 22125091HCID 22125091, compound

Product 1

HCID 22125188N-[2-(3-aminophenyl)-1,1-dimethyl-ethyl]-acetamideYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3.5 g (11 mmol) of N-[2-(4-bromo-3-nitrophenyl)-1,1-dimethyl-ethyl]acetamide in 60 ml of ethanol was treated with 3 ml (22 mmol) of triethylamine and 500 mg of 10% palladium on charcoal. The mixture was hydrogenated at atmospheric pressure for 6 hours, filtered and evaporated. The residue was partitioned between 60 ml of ethyl acetate and 60 ml of saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and evaporated to give 1.7 g (75%) of N-[2-(3-aminophenyl)-1,1-dimethyl-ethyl]-acetamide as an orange gum. [Mass spectrum (ESI) MH+ =207].

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was partitioned between 60 ml of ethyl acetate and 60 ml of saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-67723c205e5d45fd9b999782358046aa
Source dataset
uspto-grants-2000_11
Patent number
US06150373

Reaction notes

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