HCID 178487720, compound → Isoxazolo(4,5-c)quinolin-3(2H)-one, 7-methoxy-2-phenyl-

HRID 280110Notes

Reaction equation

HRID 280110 reaction equation
O[N:2]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[O:4]>O>[CH3:17][O:16][C:10]1[CH:11]=[CH:12][C:13]2[C:14]3[O:15][N:2]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:3](=[O:4])[C:5]=3[CH:6]=[N:7][C:8]=2[CH:9]=1

Participants

3

Reactant 1

HCID 178487720HCID 178487720, compound

Product 1

HCID 13669238Isoxazolo(4,5-c)quinolin-3(2H)-one, 7-methoxy-2-phenyl-Yield 20.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Using the procedure of Step B of Example 2, 3.68 g of N,4-dihydroxy-7-methoxy-N-phenyl-3-quinoline carboxamide were reacted and after 18 hours at ambient temperature, the reaction mixture was poured into water and the products which crystallized were extracted with dichloromethane. The organic phase was washed with water and the solvent was eliminated. The residue was chromatographed on silica and eluted with a mixture of methylene chloride-ethyl acetate (9-1) to obtain 0.7 g of 7-methoxy-2-phenylisoxazolo(4,5-c)quinolin-3-(2H)-one melting at 170° C.

Workup

  1. customwere reacted and after 18 hours at ambient temperature
  2. customthe products which crystallized
  3. extractionwere extracted with dichloromethane
  4. washThe organic phase was washed with water
  5. customThe residue was chromatographed on silica
  6. washeluted with a mixture of methylene chloride-ethyl acetate (9-1)

Sources & evidence

ORD record
ord-60f56b67aef84d349a812300cd540fd3
Source dataset
uspto-grants-1986_05
Patent number
US04588731

Reaction notes

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