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

HRID 1668974Notes

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-8d2fb9bc1a9447b18ca832413a9ab912
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989461B2

Reaction notes

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