P-Anisidine → HCID 11485953, compound

HRID 2113764Notes

Reaction equation

Cl[C:2]1[C:3](=[O:21])[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[CH:26][CH:25]=1>CN(C=O)C>[CH3:22][O:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][C:2]2[C:3](=[O:21])[N:4]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:5](=[O:13])[C:6]=2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:26][CH:25]=1

Participants

Conditions

Temperature: 150 °C

Procedure

3-Chloro-4-phenyl-1-(pyridin-2-ylmethyl)-1H-pyrrole-2,5-dione (2.39 mmol, 714 mg) and 4-methoxyaniline (5.26 mmol, 648 mg) were dissolved in DMF (4 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 710 mg (77%) of the title compound. 1H NMR (400 MHz, CDCl3): 8.60-8.57 (m, 1H), 7.71-7.65 (m, 1H), 7.36-7.30 (m, 1H), 7.24 (bs, 1H), 7.23-7.19 (m, 1H), 7.13-7.05 (m, 3H), 7.04-6.99 (m, 2H), 6.64-6.53 (m, 4H), 4.95 (s, 2H), 3.70 (s, 3H).

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-506a8ab7d1c04d3d9b8ca3c60a62a93f
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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