Diethyl (ethoxymethylene)malonate → Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 535471Notes

Reaction equation

CCO[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:25]2[N:33]3[C:28]([CH:29]=[CH:30][CH:31]=[CH:32]3)=[CH:27][C:26]=2[CH3:34])=[O:24])=[CH:19][CH:18]=1.C(OC(C)C)(C)C>C1(C)C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:34][C:26]1[CH:27]=[C:28]2[N:33]([C:25]=1[C:23]([C:20]1[CH:21]=[C:22]3[C:17](=[CH:18][CH:19]=1)[NH:16][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]3=[O:13])=[O:24])[CH:32]=[CH:31][CH:30]=[CH:29]2

Participants

Conditions

Temperature: 110 °C

Procedure

1.69 ml of diethyl ethoxymethylene malonate are added, under an inert atmosphere at ambient temperature, to 1.83 g (6.8 mmol) of (4-aminophenyl)(2-methylindolizin-3-yl)methanone in 23 ml of toluene. The reaction medium is heated at 110° C. for 1 h 45 and then concentrated under reduced pressure. The residue obtained is dissolved in 45 ml of diphenyl ether and then heated at 230° C. for 30 minutes. After the addition of diisopropyl ether at ambient temperature, the precipitate formed is filtered off, rinsed with diisopropyl ether, with methanol and then with dichloromethane, and dried under reduced pressure at 50° C. overnight 1.2 g of a yellow powder are obtained.

Workup

concentrationconcentrated under reduced pressure
customThe residue obtained
temperatureheated at 230° C. for 30 minutes
customthe precipitate formed
filtrationis filtered off
washrinsed with diisopropyl ether, with methanol
dry with materialwith dichloromethane, and dried under reduced pressure at 50° C. overnight 1.2 g of a yellow powder
customare obtained

Sources & evidence

ORD record: ord-87f3b63dde16412587c986174b51708d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859544B2

Reaction notes

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