Diethyl (ethoxymethylene)malonate → HCID 12852663, compound

HRID 1156831Notes

Reaction equation

HRID 1156831 reaction equation
[NH2:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1.C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C(Cl)Cl.C(OCC)(=O)C>[CH2:18]([O:17][C:15](=[O:16])[C:14](=[CH:13][NH:1][C:2]1[C:3](=[O:9])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:19]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 226342-Aminocyclohepta-2,4,6-trien-1-one

Product 1

HCID 12852663HCID 12852663, compound

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A mixture of 2-amino-2,4,6-cycloheptatrien-1-one [2 g, described by W. Von E. Doering and L. H. Knox, J. Amer. Chem. Soc., 73, 828 (1951)]and diethyl ethoxymethylenemalonate (20 ml) was heated at 140° C. for 2 hr. The reaction was cooled and subjected to chromatography on silica gel using methylene chloride-ethyl acetate (4:1) as the eluant. The pure fractions were pooled to give 4.13 g of 2-[(7-oxo-1,3,5-cycloheptatrien-1-yl)aminomethylene]-propanedioic acid diethyl ester; mp 66°-68° C.; nmr (CDCl3) δ1.35 (m, 6H), 4.35 (m, 2H), 7.35 (m, 5H), 8.4 (d, 1H), 11.4 (broad, 1H); ir (CHCl3) 3230, 1700, 1665, 1580 cm-1 ; uvλmax (MeOH) 356 nm (ε13,770), 292 (9,880), 277 (10,680), 213 (17,020) with shoulders at 338 and 236 nm.

Workup

  1. temperatureThe reaction was cooled

Sources & evidence

ORD record
ord-7cdc0890a40a4abe9bc3d75d01ebc51c
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

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