Hydrochloric Acid → HCID 23368442, compound

HRID 1901650Notes

Reaction equation

HRID 1901650 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:16][CH:17]=O)[CH2:13][CH2:14][CH3:15])[C:6]=2[CH:19]=1.B#B.Cl.[OH-].[Na+]>O1CCCC1.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([O:10][CH2:11][CH:12]([NH:16][CH3:17])[CH2:13][CH2:14][CH3:15])[C:6]=2[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 6328200DiboronHCID 23368378HCID 23368378, compound

Product 1

HCID 23368442HCID 23368442, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1 g of 5-chloro-3-(2-formylaminopentyloxy)-1,2-benzoisoxazole in 10 ml of tetrahydrofuran is dropwise added 10.1 ml of a tetrahydrofuran solution (1.0M) of diborane with ice-cooling over ten minutes, and they are further subjected to reaction at room temperature for one hour. Subsequently, 5 ml of methanol is added with ice-cooling, and thereafter, 10 ml of 6N hydrochloric acid is added thereto, and after stirring for one hour, the solvent is removed by distillation under reduced pressure. Ethyl acetate and water are added to the residue obtained, the pH is adjusted to 8 with a 10% (w/w) aqueous sodium hydroxide solution, and the organic layer is separated. The separated organic layer is washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and thereafter concentrated to about 20 ml under reduced pressure. Thereto is added 5 ml of a dioxane solution (2.2N) of hydrogen chloride, and the crystals precipitated are collected by filtration, to obtain 0.6 g of colorless, crystalline 5-chloro-3-(2-methylaminopentyloxy)-1,2-benzoisoxazole hydrochloride having a melting point of 152.9°-154.8° C.

Workup

  1. temperaturecooling over ten minutes
  2. customthey are further subjected to reaction at room temperature for one hour
  3. temperaturecooling
  4. customthe solvent is removed by distillation under reduced pressure
  5. additionEthyl acetate and water are added to the residue
  6. customobtained
  7. customthe organic layer is separated
  8. washThe separated organic layer is washed with a saturated saline solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated to about 20 ml under reduced pressure
  11. additionThereto is added 5 ml of a dioxane solution (2.2N) of hydrogen chloride
  12. customthe crystals precipitated
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-0a1092646458439b854aaa88fbde8812
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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