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

HRID 641133ノート

反応式

HRID 641133 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-252296e455384511b0f115e6e41e8d2f
出典データセット
uspto-grants-2010_04
特許番号
US07695980B2

反応ノート

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