Hydrochloric Acid → 3-(2-Amino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride

HRID 1901647Notes

Reaction equation

HRID 1901647 reaction equation
C(OC([NH:8][CH:9]([CH2:22][C:23]#[N:24])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=O)(C)(C)C.CC(O)C.Cl.C(OC(C)C)(C)C>CO>[ClH:21].[NH2:8][CH:9]([CH2:22][C:23]#[N:24])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=2[O:14][N:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 7914Diisopropyl EtherHCID 233685283-(2-Tert-butoxycarbonylamino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole

Product 1

HCID 233684313-(2-Amino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 1.0 g of 3-(2-tert-butoxycarbonylamino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole in 15 ml of methanol is added 7.8 ml of a 2-propanol solution (6.5M) of hydrogen chloride at room temperature, and they are subjected to reaction at the same temperature for seven hours. Thereafter, the solvent is removed by distillation under reduced pressure. To the residue obtained is added diisopropyl ether, and the crystals precipitated are collected by filtration, to obtain 0.78 g of colorless, crystalline 3-(2-amino-3-cyanopropoxy)-5-chloro-1,2-benzoisoxazole hydrochloride having a melting point of 188.8°-190.9° C. (decomp.).

Workup

  1. customthey are subjected to reaction at the same temperature for seven hours
  2. customThereafter, the solvent is removed by distillation under reduced pressure
  3. customTo the residue obtained
  4. customthe crystals precipitated
  5. filtrationare collected by filtration

Sources & evidence

ORD record
ord-1c4d6d544f1e4798b912a69b9d8488f1
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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