Ammonium Chloride → 9-Chloro-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione

HRID 52558

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[Cl-:22].[NH4+]>CS(C)=O>[Cl:22][C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20][CH3:21])=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Komponenten

Reaktionsbedingungen

Temperatur: 160 °C

Versuchsvorschrift

A mixture of 9-bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (530 mg, 1.50 mmol) and cuprous chloride (1.0 g, 10.1 mmol) in dimethyl sulfoxide (5 mL) was heated at 160° C. for 4.5 h and poured into 1N aqueous ammonium chloride (200 mL). The mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL). The extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL), dried over magnesium sulfate, and concentrated. The residue was recrystallized from ethanol to give 125 mg of the title compound (27%): mp 218°~220° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.08 (bs, 1H), 7.08 (d, 1H, J=2 Hz), 7.02 (d, 1H, J=2 Hz), 5.04~5.13 (m, 1H), 3.62 (s, 3H), 2.94 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.78 (dm, 1H, J=17.1 Hz), 2.63 (dd, 1H, J=18, 7.2 Hz), 2.57 (dd, 1H, J=18, 3.6 Hz), 2.09 (dm, 1H, J=13.5 Hz), 1.80~1.95 (m, 1H).

Aufarbeitung

extractionThe mixture was extracted with a mixed solvent of THF and ethyl acetate (600 mL)
washThe extract was washed with 1N aqueous ammonium chloride (200 mL×2) and brine (200 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag: ord-acbea572fe024405bccd2992d32e15b5
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05616586

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