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

HRID 280108

反応式

HRID 280108 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
5 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-769b44905db54d1fb528b59d7b4a14de
出典データセット
uspto-grants-1986_05
特許番号
US04588731

関連ノート

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