6-nitro-3H-benzo[1,2,3]oxathiazole 2,2-dioxide → 6-Amino-3H-benzo[1,2,3]oxathiazole 2,2-dioxide

HRID 413338Notes

Reaction equation

HRID 413338 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[NH:8][S:9](=[O:12])(=[O:11])[O:10][C:6]=2[CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]2[NH:8][S:9](=[O:12])(=[O:11])[O:10][C:6]=2[CH:5]=1

Participants

4

Reactant 1

HCID 52471556-nitro-3H-benzo[1,2,3]oxathiazole 2,2-dioxide

Product 1

HCID 129716986-Amino-3H-benzo[1,2,3]oxathiazole 2,2-dioxide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 6-nitro-3H-benzo[1,2,3]oxathiazole 2,2-dioxide (example 5) (8.1 g, 37 mmol) in methanol (250 ml) is hydrogenated at atmospheric pressure in the presence of Pd-C. The catalyst is then filtered off, the clear solution is treated with methanolic HCl (1 N) and the solvent is distilled off under reduced pressure. The residue is dissolved in ethanol and the product crystallizes after addition of diethyl ether.

Workup

  1. filtrationThe catalyst is then filtered off
  2. additionthe clear solution is treated with methanolic HCl (1 N)
  3. distillationthe solvent is distilled off under reduced pressure
  4. dissolutionThe residue is dissolved in ethanol
  5. customthe product crystallizes
  6. additionafter addition of diethyl ether

Sources & evidence

ORD record
ord-fcbf13ea7a5142ffb9dfbea974bd61e3
Source dataset
uspto-grants-2003_05
Patent number
US06566390B2

Reaction notes

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