N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamide → 1-(4-methoxyphenyl)-5,6-dihydropyridin-2(1H)-one

HRID 564384Notes

Reaction equation

HRID 564384 reaction equation
[CH2:1]([N:5]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:6](=[O:9])[CH:7]=[CH2:8])[CH2:2]C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([N:5]2[CH2:1][CH2:2][CH:8]=[CH:7][C:6]2=[O:9])=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 67004663N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamide

Product 1

HCID 670050131-(4-methoxyphenyl)-5,6-dihydropyridin-2(1H)-oneYield 99.7%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of N-but-3-en-1-yl-N-(4-methoxyphenyl)acrylamide (180 mg, 0.78 mmol) in degassed methylene chloride (200 mL) was added Grubbs catalyst (32 mg, 0.039 mmol) and the mixture was heated to 40° C. overnight. All volatiles were removed and the resulting material was subjected to flash chromatography (Hexanes:EtOAc 1:1) to yield 1-(4-methoxyphenyl)-5,6-dihydropyridin-2(1H)-one (158 mg, 98%).

Workup

  1. customAll volatiles were removed

Sources & evidence

ORD record
ord-93f3b81a7a8b4863b9c90b2e0dfd89f6
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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