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

HRID 1467651노트

반응식

HRID 1467651 반응식
[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]

참가 물질

6

반응물 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 7749Ethyl Propionate용매

실험 절차

(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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-e1797c4488a44dcaa10f60f7c355f826
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999987B2

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