Sodium Hydroxide → 3-(2-Amino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

HRID 1901594Notes

Reaction equation

HRID 1901594 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH:5]([CH2:18][O:19]C(=O)C1C=CC=CC=1)[CH2:6][O:7][C:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[O:10][N:9]=1>CO>[NH2:4][CH:5]([CH2:18][OH:19])[CH2:6][O:7][C:8]1[C:12]2[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=2[O:10][N:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 233684333-(2-Amino-3-benzoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride

Product 1

HCID 153825803-(2-Amino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.00 g of sodium hydroxide in 77 ml of methanol is added 7.66 g of 3-(2-amino-3-benzoyloxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride at 20°-25° C., and they are subjected to reaction at the same temperature for ten minutes. The solvent is removed from the reaction mixture by distillation under reduced pressure, and ethyl acetate and water are added to the residue obtained, and after shaking, the organic layer is separated. The separated organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure to obtain 4.13 g of colorless, crystalline 3-(2-amino-3-hydroxypropoxy)-5-chloro-1,2-benzoisoxazole.

Workup

  1. customthey are subjected to reaction at the same temperature for ten minutes
  2. customThe solvent is removed from the reaction mixture by distillation under reduced pressure, and ethyl acetate and water
  3. additionare added to the residue
  4. customobtained
  5. customthe organic layer is separated
  6. washThe separated organic layer is washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customafter which the solvent is removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-054a92c6e20641c6a30da77814937a03
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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