Diethyl (ethoxymethylene)malonate → HCID 68412103, compound

HRID 1931312Notes

Reaction equation

C([C:3]1[CH:8]=[CH:7][N+:6]([O-:9])=[C:5](CC)[C:4]=1[NH2:12])C.C(O[CH:16]=[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:18]([O:20][CH2:21][CH3:22])=[O:19])C>C(O)C>[CH2:21]([O:20][C:18](=[O:19])[C:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][NH:12][C:4]1[CH:5]=[N+:6]([O-:9])[CH:7]=[CH:8][CH:3]=1)[CH3:22]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of diethyl 3-aminopyridine 1-oxide (3.0 g, 27.3 mmol) and diethyl 2-(ethoxymethylene)malonate (11.8 g, 54.6 mmol) was heated to 130° C. under a Dean-Stark trap for 2 hours. After cooling to room temperature, the mixture was stirred with ethanol (100 mL). The solid was collected by filtration, washed with petroleum ether (100 mL) and dried in vacuo to afford the title compound (6.0 g). 1H NMR (400 MHz, MeOD) δ 8.40-8.39 (t, J=1.6 Hz, 1H), 8.36 (s, 1H), 8.01 (d, J=6.4 Hz, 1H), 7.49 (d, J=1.2 Hz, 1H), 7.46-7.44 (m, 1H), 4.22 (q, J=7.2 Hz, 2H), 4.14 (q, J=7.2 Hz, 2H), 1.08 (t, J=7.2 Hz, 6H).

Workup

temperatureAfter cooling to room temperature
filtrationThe solid was collected by filtration
washwashed with petroleum ether (100 mL)
customdried in vacuo

Sources & evidence

ORD record: ord-9bc6c21dabad4db088b20a8c44a576ad
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188283B2

Reaction notes

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