Aniline → 1H-Pyrrole-2,5-dione, 3-phenyl-4-(phenylamino)-1-(3-pyridinylmethyl)-

HRID 2113760Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 3-chloro-4-phenyl-1-(pyridin-3-ylmethyl)-1H-pyrrole-2,5-dione (0.25 mmol, 75 mg) in DMF (0.5 mL) was added aniline (0.55 mmol, 51 mg). 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 38 mg (43%) of the title compound. 1H NMR (400 MHz, CDCl3) δ 8.72 (bs, 1H), 8.54 (d, br, 1H), 7.79-7.75 (m, 1H), 7.47 (bs, 1H), 7.29-7.23 (m, 1H), 7.17-7.06 (m, 3H), 7.04-6.93 (m, 5H), 6.66-6.60 (m, 2H), 4.79 (s, 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-9f7f1a9f56f84cb4a83eb7f59432e423
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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