4-cyclopropyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide → 7-amino-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 17840Notes

Reaction equation

HRID 17840 reaction equation
[CH:1]1([N:4]2[C:9]3[CH:10]=[CH:11][C:12]([N+:14]([O-])=O)=[CH:13][C:8]=3[S:7](=[O:18])(=[O:17])[N:6]=[CH:5]2)[CH2:3][CH2:2]1>C(O)C.[Pd]>[NH2:14][C:12]1[CH:11]=[CH:10][C:9]2[N:4]([CH:1]3[CH2:2][CH2:3]3)[CH:5]=[N:6][S:7](=[O:18])(=[O:17])[C:8]=2[CH:13]=1

Participants

4

Reactant 1

HCID 675307714-cyclopropyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide

Product 1

HCID 675289727-amino-4-cyclopropyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-cyclopropyl-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide (5 g; prepared in Step C of Example 41) in ethanol (180 mL) there is added 10 % palladium-on-carbon (500 mg). The suspension is placed in a hydrogenator under 10 atmospheres of H2 for 30 minutes at ambient temperature. The suspension is concentrated to dryness under reduced pressure and the residue is taken up in boiling acetone (300 mL). The insoluble material is removed by filtration in the hot state and is washed with boiling acetone. The filtrate is concentrated to dryness and the residue is recrystallised from methanol.

Workup

  1. concentrationThe suspension is concentrated to dryness under reduced pressure
  2. customThe insoluble material is removed by filtration in the hot state
  3. washis washed with boiling acetone
  4. concentrationThe filtrate is concentrated to dryness
  5. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-31614994462e491a9d22cce00641e013
Source dataset
uspto-grants-2010_06
Patent number
US07741320B2

Reaction notes

Loading…