Diethyl (ethoxymethylene)malonate → HCID 10015075, compound

HRID 1851082Notes

Reaction equation

[NH2:1][N:2]1[CH:6]=[CH:5][CH:4]=[CH:3]1.C(O[CH:10]=[C:11]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])C>>[N:2]1([NH:1][CH:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:6]=[CH:5][CH:4]=[CH:3]1

Participants

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonate

HCID 1365891-Aminopyrrole

Product 1

HCID 10015075HCID 10015075, compound

Conditions

Temperature: 125 °C

Procedure

A mixture of N-aminopyrrole (6.2 g, 75.5 mmol) and diethyl ethoxymethylenemalonate (18.2 mL, 90.6 mmol) was heated at 125° C. for 2 hours to give diethyl 2-((1H-pyrrol-1-ylamino)methylene)malonate as an intermediate and then diphenyl ether (22 mL) was added thereto. The resulting reaction mixture was heated under nitrogen atmosphere at 220° C. for 2 hours and ethanol produced during the reaction was removed by distillation. The reaction mixture with ethanol removed was cooled to room temperature and purified by silica gel chromatography. The target compound was yielded as a yellow solid (11.0 g, 53.3 mmol, 71% yield).

Sources & evidence

ORD record: ord-a391657bc8a641878dde1cb5e6b92e04
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957102B2

Reaction notes

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