Dimethyl Sulfoxide → 1-Hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone

HRID 1387284Notes

Reaction equation

[CH2:1]([N:7]1[CH:12]=[C:11](I)[C:10]([CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:19]([O-:22])(=[O:21])C.[K+].[CH3:24]S(C)=O>CO.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([N:7]1[CH:12]=[C:11]([C:19]([O:22][CH3:24])=[O:21])[C:10]([CH3:14])=[C:9]([N+:15]([O-:17])=[O:16])[C:8]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 1-hexyl-5-iodo-4-methyl-3-nitro-2-pyridone (0.500 g, 1.37 mmol), tris(dibenzylideneacetone)dipalladium (0.003 g), diphenylphosphinoferrocene (0.154 g) and potassium acetate (0.565 g) in DMSO (10 ml,) and methanol (10 mL) was stirred and heated at 60° C. under an atmosphere of carbon monoxide for 4 hours. The mixture was diluted with ethyl acetate, washed with aqueous sodium bicarbonate, dried (MgSO4), filtered, and evaporated. Chromatography of the residue over silica gel (30% ethyl acetate/petroleum ether) gave 1-hexyl-4-methyl-3-nitro-5-methoxycarbonyl-2-pyridone (0.305 g, 75%).

Workup

washwashed with aqueous sodium bicarbonate
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-e5806ef9464d4c1f99618ffc6fda81f7
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06268365B1

Reaction notes

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