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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 343313Generated: October 29, 2026

Dimethyl 3-aminoglutaconate → Dimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-(2-phenylethyl)-1,4-dihydropyridine-3,5-dicarboxylate

https://huagongshe.com/reaction/343313

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl 3-aminoglutaconateHCID 253819—
ReactantMethyl 2-(2,6-dichlorophenylmethylidene)-3-oxo-5-phenylpentanoateHCID 53937813—
SolventDichloromethane ethylacetateHCID 21226138—
ProductDimethyl 4-(2,6-dichlorophenyl)-2-methoxycarbonylmethyl-6-(2-phenylethyl)-1,4-dihydropyridine-3,5-dicarboxylateHCID 70203360—

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of methyl 2-(2,6-dichlorophenylmethylidene)-3-oxo-5-phenylpentanoate (the crude product from the preceding experiment) and dimethyl 2-amino-1-propene-1,3-dicarboxylate (8.4 g, 48.5 mmol) was heated without solvent at 120° C. for 18 h. TLC showed a strong fluorescent spot at Rf=0.3 (dichloromethane/ethyl acetate: 24/1). This whole was chromatographed on silica gel (1.5 kg ) to yield 3.93 g of product. The slightly less pure product (2 g) was also obtained. 1H NMR (CDCl3) δ 7.23 (m, 7H), 6.99 (t, J=8.6 Hz, 1H), 6.93 (br. s, 1H), 5.98 (s, 1H), 3.70 (s, 3H), 3.68 (ABq, J=17Hz, 2H), 3.58 (s, 3H), 3.52 (s, 3H), 2.91 (m, 4H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05861402
Source datasetuspto-grants-1999_01
ORD IDord-625ecdeb49dd46df9e73d3752ce9310b
Source noteuspto-grants-1999_01