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

HRID 280109Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-9301a79aaf864eb5867b3fa139b9f8bc
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04588731

Reaction notes

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