N-Phenylhydroxylamine → Isoxazolo(4,5-c)quinolin-3(2H)-one, 2-phenyl-

HRID 280108

반응식

HRID 280108 반응식
[C:1]1([NH:7][OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[C:22](OCC)=[O:23]>O1CCCC1>[C:1]1([N:7]2[C:22](=[O:23])[C:13]3[CH:14]=[N:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 7518N-PhenylhydroxylamineHCID 24758Sodium hydrideHCID 268963Ethyl 4-Chloroquinoline-3-carboxylate

생성물 1

HCID 13564503Isoxazolo(4,5-c)quinolin-3(2H)-one, 2-phenyl-수율 5.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
5 °C

실험 절차

A solution of 9 g of N-phenylhydroxylamine [described in Organique Synthese, Vol. 1, p. 445]was added dropwise at 0° C. with stirring under an inert atmosphere to a suspension of 3.85 g of 50% sodium hydride in 100 ml of tetrahydrofuran, and after stirring at 5° C. for 30 minutes, a solution of 18.8 g of ethyl 4-chloro-3-quinoline carboxylate in 100 ml of tetrahydrofuran was added at 0° C. The mixture was stirred for 16 hours at ambient temperature and after concentration to dryness under reduced pressure, the residue was taken up in ice. The mixture was extracted with methylene chloride and the organic phase was washed, dried, and concentrated to dryness. The residue was purified by chromatography on silica (eluent: ethyl acetate) to obtain 1.2 g of 2-phenylisoxazolo(4,5-c)quinolin-3-(2H)-one (corresponding to the 3rd eluted fraction) melting at 163° C. after crystallization from isopropyl ether.

후처리

  1. addition445]was added dropwise at 0° C.
  2. stirringThe mixture was stirred for 16 hours at ambient temperature
  3. concentrationafter concentration to dryness under reduced pressure
  4. extractionThe mixture was extracted with methylene chloride
  5. washthe organic phase was washed
  6. customdried
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by chromatography on silica (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-769b44905db54d1fb528b59d7b4a14de
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588731

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