Acetic Acid → HCID 15289703, compound

HRID 37506Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])=[N:8][C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:10]([N+:17]([O-])=O)[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:5])[CH3:2].C(O)(=O)C>C(O)C>[NH2:17][C:10]1[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:8][C:7]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)(=[O:28])=[O:27])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

In 10 ml of ethanol was suspended 0.35 g of 3,4-diethoxycarbonyl-5-nitro-6-phenyl-2-(p-tolylsulfonyl)pyridine, whereto 2 ml of acetic acid and 0.15 g of reduced iron were added. The mixture was stirred at 80° C. for 4.5 hours. After ethanol was distilled off, the residue was neutralized with an aqueous solution of sodium hydrogencarbonate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over sodium sulfate, followed by concentration under reduced pressure. The residue was subjected to silica gel flash column chromatography with chloroform/ethyl acetate (4:1) as the eluent, to give 0.144 g of the title compound.

Workup

additionwere added
distillationAfter ethanol was distilled off
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over sodium sulfate
concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record: ord-d81733510f8c40759ff6e0729b255bef
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05420275

Reaction notes

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