Acetic Acid → Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate

HRID 641133노트

반응식

HRID 641133 반응식
[O:1]=[C:2]1[C:11]([CH:12]=[CH2:13])=[C:10]([C:14]([OH:16])=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[N+](=[CH2:19])=[N-].C(O)(=O)C>CO.C(OCC)C>[CH3:19][O:15][C:14]([C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:1])[C:11]=1[CH:12]=[CH2:13])=[O:16]

참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 124162522-Oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylic acid

생성물 1

HCID 12294102Methyl-2-oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylate

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

To a solution of 4.4 g (20 mmol) 2-Oxo-3-vinyl-1,2-dihydroquinoline-4-carboxylic acid 4 in 200 mL methanol was added etheral diazomethane at ambient temperature until the vigorous evolution of nitrogen subsided and the starting material was used up. Then 10 mL acetic acid were added, the mixture was diluted with 200 mL diethylether and washed with a solution of sodium bicarbonate (5%) and brine. The organic layer was separated, dried over sodium sulfate and filtered. After evaporation the crude product was purified by chromatography on silica gel eluting with toluene/ethyl acetate/methanol 4:1:1, to give 2.6 g of 5 as a pale yellow solid.

후처리

  1. washwashed with a solution of sodium bicarbonate (5%) and brine
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customAfter evaporation the crude product
  6. customwas purified by chromatography on silica gel eluting with toluene/ethyl acetate/methanol 4:1:1

출처 및 근거

ORD 기록
ord-252296e455384511b0f115e6e41e8d2f
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07695980B2

반응 노트

불러오는 중…