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

HRID 280109
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인쇄 미리보기

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HRID 280109 반응식
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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9301a79aaf864eb5867b3fa139b9f8bc
출처 데이터셋
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04588731

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