Triethylamine → 1-(4-Aminophenyl)-2-methylpropan-1-one

HRID 2378040

Reaction equation

HRID 2378040 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH:11]([CH3:13])[CH3:12])=[CH:6][CH:5]=1)([O-])=O.O.O.Cl[Sn]Cl.C(OCC)(=O)C.CCN(CC)CC>CN(C=O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:14])[CH:11]([CH3:12])[CH3:13])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 61436Stannous chloride dihydrateHCID 134452602-Methyl-1-(4-nitrophenyl)propan-1-one

Product 1

HCID 51510441-(4-Aminophenyl)-2-methylpropan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

p-Nitroisobutyrophenone from step 4 (1.0 g, 0.0058 mol), was dissolved in DMF (5 ml). SnCl2.2H2O (4.67 g, 0.0207 mol) is added and the reaction is stirred at room temperature. After 4 hours the reaction was poured into 100 ml of ethyl acetate. Excess Et3N (4 ml) was added and a white, solid precipitate formed. The suspension was filtered through celite. Evaporation of the filtrate left a yellow solid which was purified by column chromatography. The resulting crystalline solid (0.700 g, 4.2 mmol, 82%) had a 1H-NMR (DMSO): 7.71 (d, 2H), 6.58 (d, 2H), 6.03 (s, 2H), 3.45 (m, 1H), 1.06 (s, 6H)

Workup

  1. customa white, solid precipitate formed
  2. filtrationThe suspension was filtered through celite
  3. customEvaporation of the filtrate
  4. waitleft a yellow solid which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8c0c4e927cc44b928ae47bae9c1a966e
Source dataset
uspto-grants-2008_12
Patent number
US07470722B2

Linked notes

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