Hydrochloric Acid → 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile

HRID 2251643Notes

Reaction equation

[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[CH2:11][CH2:10]3)=[CH:5][CH:4]=[C:3]1[C:17]#[N:18].[I-].[Sm+3].[I-].[I-].[C:23](Cl)(=[O:25])[CH3:24].Cl>C(#N)C>[C:23]([C:5]1[CH:4]=[C:3]([C:17]#[N:18])[N:2]([CH3:1])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 120 °C

Procedure

To a stirred solution of 1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile (0.25 g, 1.0 mmol) in acetonitrile (25 mL) was added samarium iodide (0.5 g, 1.2 mmol) and acetyl chloride (1.75 mL, 24.6 mmol). The reaction mixture was heated in microwave to 120° C. for 10 minutes. The mixture was treated with a 10% aqueous HCl solution (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (30% ethyl acetate in hexane) to give 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile as a tan solid (0.025 g, 8%). MS (ESI) m/z 279; HRMS: calcd for C17H14N2O2+H+, 279.1128; found (ESI, [M+H]+), 279.1125.

Workup

extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on a silica gel column (30% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-8bf401ec560c4ccc93e2760da1f40ff4
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319152B2

Reaction notes

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