Ammonium Acetate → 2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole

HRID 456812Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=O)[CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)[CH:7]=[CH:6]2.C([O-])(=O)C.[NH4+:29]>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]1[NH:29][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:14]=1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(6-methoxy-2-naphthyl)-4-phenylbutane-1,4-dione (1.00 g, 3.14 mmol), prepared in the previous step, ammonium acetate (12.1 g, 157 mmol) and acetic acid (100 mL) was heated to 100° C. under a nitrogen atmosphere for three hours. The mixture was cooled to ambient temperature, and the precipitate was isolated by filtration to give 2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole as a white solid (0.86 g, 91%), mp 208.5–209.5° C. Elemental Analysis for C21H17NO Calc'd: C, 84.25; H, 5.72; N, 4.68. Found: C, 84.25; H, 5.77; N, 4.56.

Workup

temperatureThe mixture was cooled to ambient temperature
customthe precipitate was isolated by filtration

Sources & evidence

ORD record: ord-9c1b2a918d8a48959d4da04a055cf1da
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186749B2

Reaction notes

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