Water → HCID 13015730, compound

HRID 652888Notes

Reaction equation

HRID 652888 reaction equation
Cl[C:2]1[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=O.Cl.[NH2:20][OH:21].[H-].[Na+].O>N1C=CC=CC=1.CN(C=O)C>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4]1[C:3]2[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:2]=2[O:21][N:20]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 443297Hydroxyamine hydrochlorideHCID 14012563HCID 14012563, compound

Product 1

HCID 13015730HCID 13015730, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

2-chloro-2'-fluoro-4-methoxybenzophenone (15.5 g) is refluxed for three hours in 150 ml of pyridine containing 10.0 g of hydroxylamine hydrochloride. The pyridine is removed in vacuo and the residue is distributed between ether and 5% HCl. Drying and evaporation of the organic phase gives an isomeric mixture of oximes. The mixture is dissolved in 50 ml of DMF and is added to a suspension of 1.5 g NaH in 30 ml of DMF. After warming at 60° C. for 30 minutes the reaction mixture is poured into H2O and extracted with ether. Concentration under reduced pressure gives a solid. Recrystallization from ether gives 3-(2-fluorophenyl)-6-methoxy-1,2-benzisoxazole, mp 101°-103° C.

Workup

  1. customThe pyridine is removed in vacuo
  2. customDrying
  3. customevaporation of the organic phase
  4. customgives
  5. extractionextracted with ether
  6. concentrationConcentration under reduced pressure
  7. customgives a solid
  8. customRecrystallization from ether

Sources & evidence

ORD record
ord-c5098f88d5504c04948376db8f4960f3
Source dataset
uspto-grants-1987_06
Patent number
US04673746

Reaction notes

Loading…