P-Anisidine → 3-[(4-Methoxyphenyl)amino]-1-(3-methoxypropyl)-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113765Notes

Reaction equation

Cl[C:2]1[C:3](=[O:19])[N:4]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=1>CN(C=O)C>[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH:26][C:2]2[C:3](=[O:19])[N:4]([CH2:14][CH2:15][CH2:16][O:17][CH3:18])[C:5](=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-Chloro-1-(3-methoxypropyl)-4-phenyl-1H-pyrrole-2,5-dione (0.20 mmol, 56 mg) and 4-methoxyaniline (0.48 mmol, 59 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150° C. for five min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 11 mg (15%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 7.17 (bs, 1H), 7.14-7.05 (m, 3H), 7.01-6.95 (m, 2H), 6.63-6.52 (m, 4H), 3.71 (t, J=7.0 Hz, 2H), 3.70 (s, 3H), 3.45 (t, J=6.2 Hz, 2H), 3.34 (s, 3H), 1.94 (m, 2H).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record: ord-8d1b889584c344d79b8f9857c4ac11da
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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