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

HRID 1348682Notes

Reaction equation

HRID 1348682 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-61733a5c6fe643b98e15d0294b82eb94
Source dataset
uspto-grants-2007_05
Patent number
US07211592B2

Reaction notes

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