Diethyl Ether → Diethyl 2-((2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate

HRID 2092332Notes

Reaction equation

[NH2:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.C(O[CH:12]=[C:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15])C.CCOCC>C(O)(C)C>[O:8]=[C:3]1[C:2]([NH:1][CH:12]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:7][CH:6]=[CH:5][NH:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Aminopyridin-2(1H)-one (9.00 g, 81.7 mmol) was treated with diethyl ethoxymethylenemalonate (24.6 ml, 123 mmol) and heated to 100° C. After 3 hours, the reaction was cooled down and diluted with isopropyl alcohol. The solid that crashed out was collected by suction filtration and washed well with IPA and then ether to give diethyl 2-((2-oxo-1,2-dihydropyridin-3-ylamino)methylene)malonate (14.5 g, 63.3% yield) as a greenish solid. MS(M+H)+ 281.

Workup

temperaturethe reaction was cooled down
filtrationThe solid that crashed out was collected by suction filtration
washwashed well with IPA

Sources & evidence

ORD record: ord-5259ed6de34a408abab69647f7dedecb
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

Loading…