Nitrogen → 7-Chloro-3-(2,3-difluorophenyl)-6-methoxy-1,2-benzisoxazole

HRID 568663Notes

Reaction equation

HRID 568663 reaction equation
[H-].[Na+].C(O/[N:7]=[C:8](/[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[F:26])\[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([Cl:17])[C:10]=1[OH:18])(=O)C.N#N.O>CN(C=O)C>[Cl:17][C:11]1[C:10]2[O:18][N:7]=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=3[F:26])[C:9]=2[CH:14]=[CH:13][C:12]=1[O:15][CH3:16]

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 24758Sodium hydrideHCID 136477386[(E)-[(3-chloro-2-hydroxy-4-methoxyphenyl)-(2,3-difluorophenyl)methylidene]amino] acetate

Product 1

HCID 140124987-Chloro-3-(2,3-difluorophenyl)-6-methoxy-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
45 °C

Procedure

To a mixture of 1.4 g of NaH in 200 ml of DMF, a solution of 19 g of E-3-chloro-2',3'-difluoro-2-hydroxy-4-methoxybenzophenone O-acetyl oxime in 200 ml of DMF is added dropwise in an atmosphere of N2. The mixture is stirred for one half hour and then warmed at 45° C. for one half hour. Water is added and a product precipitates and is filtered and dried giving 7-chloro-3-(2,3-difluorophenyl)-6-methoxy-1,2-benzisoxazole, mp 184°-189° C.

Workup

  1. customa product precipitates
  2. filtrationis filtered
  3. customdried

Sources & evidence

ORD record
ord-d15a806a1c544e8691727a6a8156f668
Source dataset
uspto-grants-1988_03
Patent number
US04728662

Reaction notes

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