3-Aminopyridine → 3-Amino-1-[4-(4-chlorophenyl)-2,5-dioxo-1H-pyrrol-3-yl]pyridinium chloride

HRID 2084995Notes

Reaction equation

[Cl:1][C:2]1[C:3](=[O:15])[NH:4][C:5](=[O:14])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[NH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1>C1COCC1>[Cl-:1].[NH2:16][C:17]1[CH:18]=[N+:19]([C:2]2[C:3](=[O:15])[NH:4][C:5](=[O:14])[C:6]=2[C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[CH:20]=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione (100 mg, 0.41 mmol) and 3-aminopyridine (42.7 mg, 0.45 mmol) in dry THF (2.5 mL) was heated at 50° C. for 2 hours then stirred at room temperature overnight. The resulting suspension was filtered and the solid washed with dichloromethane (20 mL), then hexane (10 mL) to give the title compound as a solid.

Workup

filtrationThe resulting suspension was filtered
washthe solid washed with dichloromethane (20 mL)

Sources & evidence

ORD record: ord-56bdb6de759049d89c6174ccef0feb4a
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06719520B2

Reaction notes

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