Diethyl (ethoxymethylene)malonate → HCID 10015075, compound

HRID 2117073Notes

Reaction equation

HRID 2117073 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

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 1365891-Aminopyrrole

Product 1

HCID 10015075HCID 10015075, compound

Procedure

A mixture of N-aminopyrrole (575 mg, 7.0 mmol, commercially available) and diethyl ethoxymethylenemalonate (1.82 g, 8.4 mmol) was heated at 125° C. for 2 hours to give crude diethyl 2-((1H-pyrrol-1-ylamino)methylene)malonate. To this intermediate was added diphenyl ether (2 mL). The reaction was put under nitrogen and heated at 220° C. for 2 hours, while allowing the ethanol formed in the reaction to be distilled off. The reaction was cooled to room temperature and purified by silica gel flash chromatography (eluted with 100% CH2Cl2) to give the title compound (1.03 g, 71%) as a yellow solid.

Sources & evidence

ORD record
ord-b44655e7819d483392901df3dbfd0174
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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