Trifluoroacetic acid → (7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde

HRID 385510ノート

反応式

HRID 385510 の反応式
[O:1]1CCO[CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[N:15]=2)[CH:10]=[CH:9][C:8]1=[O:19].FC(F)(F)C(O)=O>O>[CH3:18][O:17][C:14]1[N:15]=[C:16]2[C:11]([CH:10]=[CH:9][C:8](=[O:19])[N:7]2[CH2:6][CH:2]=[O:1])=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 578153441-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one

生成物 1

HCID 57815463(7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde収率 77.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
66 °C

実験手順

To 2.8 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-1,8-naphthyridin-2(1H)-one, 20 mL of an 80% aqueous trifluoroacetic acid solution was added, and the mixture was stirred at 60 to 72° C. for 3 hours 20 minutes, and at 80 to 85° C. for 2 hours 20 minutes, 4 mL of water was then added thereto and the mixture was further stirred for 4 hours. The reaction mixture was cooled to room temperature and then left overnight, and the solvent was distilled off under reduced pressure. To the resultant residue, a saturated aqueous sodium hydrogen carbonate solution and chloroform were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.8 g of (7-methoxy-2-oxo-1,8-naphthyridin-1(2H)-yl)acetaldehyde as a yellow solid.

後処理

  1. stirringthe mixture was further stirred for 4 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. waitleft overnight
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the resultant residue, a saturated aqueous sodium hydrogen carbonate solution and chloroform were added
  6. customthe organic layer was separated
  7. extractionthe aqueous layer was extracted with chloroform
  8. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-35f0aee96f7847838b4cb16ac581186a
出典データセット
uspto-grants-2013_02
特許番号
US08367831B2

反応ノート

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