2,2-Dimethyl-1,3-dioxane-4,6-dione → 2-hydroxy-4H-quinolizin-4-one-3carboxylic

HRID 255602

반응식

HRID 255602 반응식
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=O.CC1(C)[O:18][C:17](=O)[CH2:16][C:15](=[O:20])[O:14]1>CN(C)C=O>[OH:11][C:9]1[CH:8]=[C:3]2[N:2]([C:17](=[O:18])[C:16]=1[C:15]([OH:20])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4]2

참가 물질

4

반응물 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 853172-Pyridineacetic acid, hydrochloride (1:1)

생성물 1

HCID 566055562-hydroxy-4H-quinolizin-4-one-3carboxylic수율 18.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of pyridin-2-ylacetic acid hydrochloride (1 g) in N,N-dimethylformamide (10 ml) was added N,N'-carbonyldiimidazole (934 mg) at room temperature and the mixture was heated at 60° C. for 20 minutes. To the mixture was added 2,2-dimethyl-1,3-dioxane-4,6-dione (830 mg) at 60° C. and the mixture was stirred for 1 hour at the same temperature. The solvent was distilled off and the residue was diluted with chloroform and washed with water. The chloroform layer was extracted with aqueous sodium hydrogen carbonate and the aqueous layer was washed with chloroform and acidified to pH 2 with 6N hydrochloric acid at 0° C. and extracted with chloroform. The chloroform layer was washed with brine, dried over magnesium sulfate, and evaporated to give 2-hydroxy-4H-quinolizin-4-one-3carboxylic acid (220 mg).

후처리

  1. distillationThe solvent was distilled off
  2. additionthe residue was diluted with chloroform
  3. washwashed with water
  4. extractionThe chloroform layer was extracted with aqueous sodium hydrogen carbonate
  5. washthe aqueous layer was washed with chloroform
  6. customacidified to pH 2 with 6N hydrochloric acid at 0° C.
  7. extractionextracted with chloroform
  8. washThe chloroform layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated

출처 및 근거

ORD 기록
ord-812869e4d1b344eca4ff22f5cbb406ea
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04698349

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