Acetic Anhydride → 5-[2-(2,4-Dichloro-phenyl)-acryloyl]-1H-pyridin-2-one

HRID 333863Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:12]1[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=1)=[O:11].[C:19](OC(=O)C)(=O)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:19])[C:10]([C:12]1[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5-[2-(2,4-dichloro-phenyl)-acetyl]-1H-pyridin-2-one (800 mg) in CH2Cl2 (2.8 ml) was added N,N,N′N′-tetramethyldiaminomethane (896 mg). The mixture was cooled to 0° C. and acetic acid anhydride (0.64 ml) was added. The mixture was stirred at 0° C. for 10 min and at room temperature for 4 h. The solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc and washed with water. The organic phase was concentrated to dryness to give the title compound (857 mg) as a light brown solid that was used for the next step without further purification. MS (m/e, ISP neg. ion)=291.9 [M−H+].

Workup

customThe solvent was evaporated under reduced pressure
dissolutionThe residue was dissolved in EtOAc
washwashed with water
concentrationThe organic phase was concentrated to dryness

Sources & evidence

ORD record: ord-49dff57508284876b63f5f8308067f2e
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883786B2

Reaction notes

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