4-Methyl-5-nitrosaccharin → 4-Methyl-5-aminosaccharin

HRID 343748

Reaction equation

HRID 343748 reaction equation
[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[N+:14]([O-])=O.[H][H]>O.[Pd]>[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:14]

Participants

5

Reactant 2

HCID 153345344-Methyl-5-nitrosaccharinHCID 178418361HCID 178418361, compound

Product 1

HCID 701876914-Methyl-5-aminosaccharin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

33.6 g (0.13 mol) of 4-methyl-5-nitro-1,1,3-trioxo-2,3-dihydro-1λ6 benz[d]isothiazole are dissolved in 1.2 l of water with warming to 45° C. and 5 g of Pd/C (10 percent on active carbon) are added. Hydrogen gas is then passed in with vigorous stirring (pressureless hydrogenation). 9 l of H2 are absorbed in the course of 4.5 hours. After cooling to 25° C., the catalyst is filtered off, and the filtrate is concentrated to a volume of 200 ml (on a Rotavapor) and then acidified to pH 1. The deposited precipitate is filtered off with suction, washed with water and dried under reduced pressure at 50° C. 23.4 g (0.11 mol=85% of theory) of a white solid of m.p.: 272°-273° C. are obtained.

Workup

  1. custom9 l of H2 are absorbed in the course of 4.5 hours
  2. temperatureAfter cooling to 25° C.
  3. filtrationthe catalyst is filtered off
  4. concentrationthe filtrate is concentrated to a volume of 200 ml (on a Rotavapor) and
  5. filtrationThe deposited precipitate is filtered off with suction
  6. washwashed with water
  7. customdried under reduced pressure at 50° C
  8. custom23.4 g (0.11 mol=85% of theory) of a white solid of m.p.: 272°-273° C. are obtained

Sources & evidence

ORD record
ord-c2a0168562554394973e6eb710a292fe
Source dataset
uspto-grants-1999_01
Patent number
US05863864

Linked notes

Loading…