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Triphenylphosphine → Isoxazolo(4,5-c)quinolin-3(2H)-one, 8-fluoro-2-phenyl-

HRID 280109
ノート
印刷プレビュー

反応式

HRID 280109 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC([O-])=O.O[N:31]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:32]([C:34]1[CH:35]=[N:36][C:37]2[C:42]([C:43]=1[OH:44])=[CH:41][C:40]([F:45])=[CH:39][CH:38]=2)=[O:33]>CN(C)C=O>[F:45][C:40]1[CH:39]=[CH:38][C:37]2[N:36]=[CH:35][C:34]3[C:32](=[O:33])[N:31]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[O:44][C:43]=3[C:42]=2[CH:41]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 86599450N-ethoxycarbonyliminocarbamateHCID 178519810N,4-dihydroxy-6-fluoro-N-phenyl-3-quinoline carboxamide

生成物 1

HCID 13669237Isoxazolo(4,5-c)quinolin-3(2H)-one, 8-fluoro-2-phenyl-収率 14.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Into a mixture of 8.81 g of triphenylphosphine and 50 ml of dimethylformamide, 5.58 g of ethyl azodicarboxylate were poured at 10°-15° C. and after continued stirring for 15 minutes, 6.68 g of the product of Step A were added in small fractions. Stirring was maintained for 2 hours at 0° C. and for 16 hours at ambient temperature and the crystallized product was separated. The filtrate was poured into iced water, and extracted with dichloromethane. The organic phase was washed with water, dried and the solvent was eliminated. The residue was chromatographed on silica and eluted with a methylene chloride-ethyl acetate mixture (9-1) to obtain 0.92 g of 8-fluoro-2-phenylisoxazolo(4,5-c)quinolin-3-(2H)-one melting at 174° C.

後処理

  1. additionwere poured at 10°-15° C.
  2. stirringStirring
  3. customthe crystallized product was separated
  4. additionThe filtrate was poured into iced water
  5. extractionextracted with dichloromethane
  6. washThe organic phase was washed with water
  7. customdried
  8. customThe residue was chromatographed on silica
  9. washeluted with a methylene chloride-ethyl acetate mixture (9-1)

出典と根拠

ORDレコード
ord-9301a79aaf864eb5867b3fa139b9f8bc
出典データセット
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04588731

反応ノート

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