p-Aminoacetophenone → N-(4-Acetylphenyl)prop-2-enamide

HRID 1595273Notes

Reaction equation

HRID 1595273 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[CH3:14])=[CH:9][CH:8]=1.CCN(CC)CC>C(Cl)Cl>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([NH:6][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:8][CH:9]=1)(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 8471TriethylamineHCID 13140Acryloyl chloride

Product 1

HCID 89743N-(4-Acetylphenyl)prop-2-enamideYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acryloyl chloride (29.5 mL, 363 mmol) in CH2Cl2 (50 mL) was added dropwise (30 min) to an ice-cold solution of 4′-aminoacetophenone (49.0 g, 363 mmol) and Et3N (50.6 mL, 363 mmol) in CH2Cl2 (300 mL). The reaction mixture was stirred at 0° for 15 min and then was concentrated under reduced pressure. The residue was dissolved with EtOAc. The solution was washed successively with 10% aqueous HCl, saturated aqueous NaHCO3 and H2O. The organic phase was dried (MgSO4) and concentrated under reduced pressure to afford the desired N-(4-acetylphenyl)-2-propenamide (52 g, 76% yield) as a yellow solid: 1H NMR (400 MHz, CDCl3) δ8.17 (broad s, 1H), 7.93 (d, J=8.9 Hz, 2H), 7.72 (d, J=8.9 Hz, 2H), 6.47 (dd, J=1.0, 16.9 Hz, 1H), 6.33 (dd, J=10.2, 16.9 Hz, 1H), 5.80 (dd, J=1.0, 10.2 Hz, 1 H), 2.58 (s, 3H); MS (FAB) m/z 190 (MH)+.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. dissolutionThe residue was dissolved with EtOAc
  3. washThe solution was washed successively with 10% aqueous HCl, saturated aqueous NaHCO3 and H2O
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7df8f8b93c6242ffb113ae57740c6b9e
Source dataset
uspto-grants-2001_09
Patent number
US06288091B1

Reaction notes

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