Ethanol → Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467651ノート

反応式

HRID 1467651 の反応式
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[N:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][O:15][C:16]3=[O:21])=[CH:6][CH:5]=1.[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.[Na].[CH2:33]([OH:35])[CH3:34]>C(OCC)(=O)CC>[CH3:23][N:2]([CH3:1])[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:30]([C:26]3[N:25]([CH3:24])[CH:29]=[CH:28][N:27]=3)[C:14](=[O:15])[C:13]3[C:17]([C:16]([O:35][CH2:33][CH3:34])=[O:21])=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11]2)=[CH:6][CH:5]=1)=[O:22]

参加物

6

反応物 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438、化合物

生成物 1

HCID 67261992Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate収率 37%

試薬・触媒・溶媒 1

HCID 7749Ethyl Propionate溶媒

実験手順

(E)-N,N-Dimethyl-4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (924 mg, 3.0 mmol), 1-methyl-1H-imidazole-2-carbaldehyde (363 mg, 3.3 mmol), sodium (276 mg, 12 mmol) in ethanol (30 mL) and ethyl propionate (45 mL) were added and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:2) to afford the title compound as a yellow solid (500 mg, yield 37%). LC-MS (ESI) m/z: 447 (M+1)+.

後処理

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1 to 1:2)

出典と根拠

ORDレコード
ord-e1797c4488a44dcaa10f60f7c355f826
出典データセット
uspto-grants-2015_04
特許番号
US08999987B2

反応ノート

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