Tetrahydrofuran → HCID 67353855, compound

HRID 75835Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.C1COCC1.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[C:13]([C:15]([NH:17][C:18](=[CH2:23])[C:19]([O:21][CH3:22])=[O:20])=[O:16])[O:12][N:11]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 2-(3-(4-nitrophenyl)isoxazole-5-carboxamido)acrylate (1.2 g, 3.78) was dissolved in EtOH (20 ml), THF (8 ml) and water (8 ml). Then ammonium chloride (601 mg, 11.34 mmol)) and iron (529 mg, 9.45) were added and refluxed at 80° C. for 1.5 hours. Reaction mixture was cooled and filtered through celite and solvent was removed under reduced pressure to get dark brown residue. Residue was taken in water and extracted with EtOAc. The organic layer was separated, dried over Na2SO4 and concentrated to get dark brown residue, which was purified by column chromatography using EtOAc and petroleum ether to yield 200 mg (18%) of the title compound. MS: ES (+): m/z 288 (M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 10.115 (s, 1H), 7.577 (d, 2H), 7.558 (s, 1H), 6.640 (d, 2H), 6.011 (s, 1H), 5.873 (s, 1H), 5.642 (s, 2H), 3.753 (s, 3H).

Workup

customReaction mixture
temperaturewas cooled
filtrationfiltered through celite and solvent
customwas removed under reduced pressure
customto get dark brown residue
extractionextracted with EtOAc
customThe organic layer was separated
dry with materialdried over Na2SO4
concentrationconcentrated
customto get dark brown residue, which
customwas purified by column chromatography

Sources & evidence

ORD record: ord-f05c31a21ef64ca2bb9cee0f6b41103d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835428B2

Reaction notes

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