Hydrochloric Acid → HCID 23368369, compound

HRID 1901616Notes

Reaction equation

HRID 1901616 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([O:12][CH2:13][CH:14]([NH:18][CH:19]=O)[CH2:15][O:16][CH3:17])[C:8]=2[CH:21]=1.Cl.[OH-].[Na+]>O1CCCC1.CC(O)C.O1CCOCC1.O.C(OCC)(=O)C.CO>[ClH:3].[CH3:19][NH:18][CH:14]([CH2:15][O:16][CH3:17])[CH2:13][O:12][C:9]1[C:8]2[CH:21]=[C:4]([Cl:3])[CH:5]=[CH:6][C:7]=2[O:11][N:10]=1

Participants

11

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 23368487HCID 23368487, compound

Product 1

HCID 23368369HCID 23368369, compound

Reagents, catalysts & solvents 6

HCID 887MethanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Under a nitrogen stream, 0.27 g of sodium borohydride and 0.86 ml of a boron trifluoride-diethyl ether complex salt are added to a solution of 0.40 g of 5-chloro-3-(2-formylamino-3-methoxypropoxy)-1,2-benzoisoxazole in 6 ml of tetrahydrofuran at -45° to -40° C. The temperature is elevated to 20°-25° C., and then, they are subjected to reaction at the same temperature for two hours. To the reaction mixture is added 15 ml of methanol with ice-cooling, and then, 0.58 ml of a dioxane solution (2.2N) of hydrogen chloride is added, after which they are stirred for ten minutes. Thereafter, the solvent is removed by distillation under reduced pressure. To the residue obtained are added ethyl acetate and water, and the pH is adjusted to 9 with a 10% (w/w) aqueous sodium hydroxide solution, after which 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. The residue obtained is dissolved in 8 ml of 2-propanol, and to this solution is added 0.70 ml of a dioxane solution (2.2N) of hydrogen chloride, after which the crystals precipitated are collected by filtration, to obtain 0.25 g of colorless, crystalline 3-(2-methylamino-3-methoxypropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 197°-198° C.

Workup

  1. customis elevated to 20°-25° C.
  2. customthey are subjected to reaction at the same temperature for two hours
  3. temperaturecooling
  4. customThereafter, the solvent is removed by distillation under reduced pressure
  5. customTo the residue obtained
  6. customafter which the organic layer is separated
  7. washThe separated organic layer is washed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customafter which the solvent is removed by distillation under reduced pressure
  10. customThe residue obtained
  11. customafter which the crystals precipitated
  12. filtrationare collected by filtration

Sources & evidence

ORD record
ord-523cfc84497f4854983bbb9e4851eeb0
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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