2-[2-Chloro-5-(methoxycarbonyl)phenylamino]-2-butenedioic acid diethyl ester → 8-Chloro-4-oxo-1,4-dihydro-2,5-quinolinedicarboxylic acid 2-ethyl 5-methyl ester

HRID 272563Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:24])[C:5]([NH:12][C:13]1[CH:18]=[C:17]([C:19]([O:21][CH3:22])=[O:20])[CH:16]=[CH:15][C:14]=1[Cl:23])=[CH:6][C:7]([O:9]CC)=O)[CH3:2]>C1(C2C=CC=CC=2)C=CC=CC=1.CCOCC>[CH3:22][O:21][C:19]([C:17]1[C:18]2[C:7](=[O:9])[CH:6]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:24])[NH:12][C:13]=2[C:14]([Cl:23])=[CH:15][CH:16]=1)=[O:20]

Participants

Conditions

Temperature: 250 °C

Procedure

A suspension of 23 (9.00 g, 25.4 mmol) in biphenyl ether (100 mL) was heated to 250° C. and stirred for 3 h. Then the reaction mixture was cooled to room temperature and purified by flash chromatography (hexanes to EtOAc) to afford a colorless oil (24, 3.88 g, 49.4%). 1H NMR (CDCl3, 300 MHz) δ 9.39 (br s, 1H), 7.75 (d, J=8.0 Hz, 1H), 7.24 (d, J=8.0 Hz, 1H), 6.96 (s, 1H), 4.54 (q, J=7.0 Hz, 2H), 4.00 (s, 3H), 1.46 (t, J=7.0 Hz, 3H).

Workup

temperatureThen the reaction mixture was cooled to room temperature
custompurified by flash chromatography (hexanes to EtOAc)
customto afford a colorless oil (24, 3.88 g, 49.4%)

Sources & evidence

ORD record: ord-a03c784ab3a7479588249be22b83c811
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07456178B2

Reaction notes

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