Ethanol → 1,2-Benzisothiazol-4-ol, 7-amino-

HRID 1449115Notes

Reaction equation

HRID 1449115 reaction equation
CO.C(O)C.C(OC(=O)C)(=O)C.[NH:13]([C:17]1[C:25]2[S:24][N:23]=[CH:22][C:21]=2[C:20]([O:26]C(=O)C)=[CH:19][CH:18]=1)C(C)=O>C(O)(=O)C.C(O)CC>[NH2:13][C:17]1[C:25]2[S:24][N:23]=[CH:22][C:21]=2[C:20]([OH:26])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 7918Acetic AnhydrideHCID 203499417-Acetamino-4-acetoxy-1,2-benzisothiazole2×

Product 1

HCID 1356171871,2-Benzisothiazol-4-ol, 7-amino-

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 10311-PropanolSolvent

Procedure

This reduction is as a rule carried out under atmospheric pressure or in a closed vessel under superatmospheric pressure, with or without simultaneous heating. The reaction may be carried out in the presence of a diluent or solvent, for example, a lower alcohol, e.g. methanol, ethanol or preferably propanol, or in the acid required for the reduction, preferably in acetic acid, or in the acylating reaction medium of acetic acid and acetic anhydride, described above, in which 7-acetamino-4-acetoxy-1,2-benzisothiazole is obtained. 7-Acetamino-4-acetoxy-1,2-benzisothiazole can subsequently be deacylated in the above manner to give 7-amino-4-hydroxy-1,2-benzisothiazole.

Workup

  1. customcarried out under atmospheric pressure or in a closed vessel under superatmospheric pressure
  2. customThe reaction
  3. customis obtained

Sources & evidence

ORD record
ord-38f6917caac942a9a95e10acc735d2e3
Source dataset
uspto-grants-1980_02
Patent number
US04189433

Reaction notes

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