Hydrochloric Acid → Ethyl 4-methyl-3-(2-nitrophenyl)-1H-pyrrole-2-carboxylate

HRID 2045720Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[C:11]([N+]([O-])=O)[CH3:12])([O-:3])=[O:2].C1CCN2C(=NCCC2)CC1.[N+:27]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])#[C-:28].Cl>C1COCC1.C(O)(C)(C)C.CCOC(C)=O>[CH3:12][C:11]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:27][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 1-nitro-2-[2-nitroprop-1-en-1-yl]benzene (4.1 g, 19.7 mmol) in a mixture of THF (131 mL) and tert-BuOH (66 mL) was treated with DBU (4.45 mL, 29.5 mmol) and ethyl isocyanoacetate (2.67 g, 2.58 mL) added. The resulting solution was stirred for 1 h, then heated to 70° C. for 4 h. The mixture was cooled and concentrated in vacuo to give residue that was taken up in EtOAc and aqueous HCl (1 N). The organic layer was separated and washed with brine, then dried over Na2SO4. Filtration and solvent removal afforded a residue that was purified on silica gel (gradient elution, 0-40% EtOAc/hexanes) to afford the title compound (3.2 g, 59%) as solid. LCMS (ES+) m/z 275 (M+H)+.

Workup

additionadded
temperatureThe mixture was cooled
concentrationconcentrated in vacuo
customto give residue that
customThe organic layer was separated
washwashed with brine
dry with materialdried over Na2SO4
filtrationFiltration and solvent removal
customafforded a residue that
customwas purified on silica gel (gradient elution, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record: ord-62377b6b61dd4a039e40b89cb95e3ddc
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08591878B2

Reaction notes

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