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

HRID 1423359Notes

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 a residue 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 a residue
customThe organic layer was separated
washwashed with brine
dry with materialthen dried 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-9d21274890354b08a8c0ebf729c45c35
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927569B2

Reaction notes

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