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

HRID 535471ノート

反応式

HRID 535471 の反応式
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

参加物

6

反応物 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 7914Diisopropyl EtherHCID 66653274(4-Aminophenyl)(2-methylindolizin-3-yl)methanone

生成物 1

HCID 66653314Ethyl 6-[(2-methylindolizin-3-yl)carbonyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 7583Diphenyl Ether溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-87f3b63dde16412587c986174b51708d
出典データセット
uspto-grants-2014_10
特許番号
US08859544B2

反応ノート

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