ethyl 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate → Ethyl 8-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxylate

HRID 22978Notes

Reaction equation

HRID 22978 reaction equation
[NH2:1][S:2][O:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:18]4[CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=[CH:23][C:17]=4[CH2:16][CH2:15][C:14]=3[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:12]2)=[CH:7][CH:6]=1.[H][H]>CN(C=O)C.[Pd]>[NH2:24][C:21]1[CH:22]=[CH:23][C:17]2[CH2:16][CH2:15][C:14]3[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:12][N:11]([C:8]4[CH:7]=[CH:6][C:5]([O:4][O:3][S:2][NH2:1])=[CH:10][CH:9]=4)[C:19]=3[C:18]=2[CH:20]=1

Participants

5

Reactant 2

HCID 22291943ethyl 1-{4-[(aminothio)peroxy]phenyl}-8-nitro-4,5-dihydro-1H-benzo[g]indazole-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22592527Ethyl 8-amino-1-{4-[(aminothio)peroxy]phenyl}-4,5-dihydro-1H-benzo[g]indazole-3-carboxylateYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

The product of Example 2 (2.0 g) and 10% Pd/C (350 mg) in DMF (20 mL) were shaken at 55 psi hydrogen for 3 hours. The catalyst was removed by filtration and the filtrate was concentrated under vacuum to yield a yellow wax. The wax was triturated with methanol and the resulting amber solid was collected by filtration to afford the title compound (1.6 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. customto yield a yellow wax
  4. customThe wax was triturated with methanol
  5. filtrationthe resulting amber solid was collected by filtration

Sources & evidence

ORD record
ord-7085d5ffcae146b2aabcf5c3aaa406b0
Source dataset
uspto-grants-2005_02
Patent number
US06849653B2

Reaction notes

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