Water → Ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate

HRID 26701

반응식

HRID 26701 반응식
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[C:8](OCC)(=O)[C:9]#[CH:10].O.[C:16]([O:19][CH2:20][CH3:21])(=[O:18])[CH3:17].[CH3:22][N:23]([CH3:26])[CH:24]=[O:25]>>[CH3:22][N:23]1[C:26]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:3]2[CH:1]=[C:17]([C:16]([O:19][CH2:20][CH3:21])=[O:18])[CH:5]=[C:4]2[C:24]1=[O:25]

참가 물질

6

반응물 5

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12182Ethyl propiolate

생성물 1

HCID 14067565Ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate수율 41%

반응 조건

온도
70 °C

실험 절차

800 mg of dry triethylamine and then 1.13 g of ethyl propiolate were added to a suspension of 2.3 g of the product of Step B in 50 ml of dimethylformamide and the mixture was heated to 70° C. and then was allowed to stand at room temperature for 2 days. 300 ml of water and 200 ml of ethyl acetate were added thereto and the mixture was stirred. The mixture was decanted and the aqueous layer was extracted twice with 50 ml of ethyl acetate. The combined organic phases were washed with water, dried and filtered. The filtrate was evaporated to dryness and oil residue was triturated with ether. The mixture was filtered to obtain a 41% yield of ethyl 5-methyl-4,5-dihydro-4-oxo-pyrrolo[1,2-a]quinoxaline-2-carboxylate which melted at 197°-198° C. after crystallization from ethyl acetate.

후처리

  1. customThe mixture was decanted
  2. extractionthe aqueous layer was extracted twice with 50 ml of ethyl acetate
  3. washThe combined organic phases were washed with water
  4. customdried
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness and oil residue
  7. customwas triturated with ether
  8. filtrationThe mixture was filtered

출처 및 근거

ORD 기록
ord-4afa53559f414ab1b60b358bf660a80d
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04151280

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