Methyl vinyl ketone → (3RS)-3-Methyl-4-N-(3-oxo-1-butyl)-3,4-dihydroquinoxalin-2(1H)-one

HRID 840570Notes

Reaction equation

HRID 840570 reaction equation
[CH3:1][CH:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12].[CH:13]([C:15]([CH3:17])=[O:16])=[CH2:14].C(N(CC)CC)C.C(OC)(C)(C)C.CCCCCCC>C(O)C>[CH3:1][CH:2]1[N:11]([CH2:14][CH2:13][C:15](=[O:16])[CH3:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:12]

Participants

6

Reactant 4

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 27636423-Methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 22389680MTBE heptane2×

Product 1

HCID 22619809(3RS)-3-Methyl-4-N-(3-oxo-1-butyl)-3,4-dihydroquinoxalin-2(1H)-oneYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Methyl-3,4-dihydroquinoxalin-2(1H)-one (0.5 g, 3.1 mmol) together with 0.35 ml (4.3 mmol) of methyl vinyl ketone and a catalytic amount of triethylamine were stirred for 20 hours at room temperature in 20 ml of anhydrous ethanol. Silica gel chromatography with methyl tert.-butyl ether/heptane=2:1 gave 620 mg (87%) of the desired product, melting point 108-109° C. (methyl tert.-butyl ether/heptane).

Sources & evidence

ORD record
ord-793258db47464266ae292ceb524aeeeb
Source dataset
uspto-grants-2002_04
Patent number
US06369057B1

Reaction notes

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