3-(methylthio)-6-nitro-1-phenyl-1H-indazole → 3-(methylthio)-1-phenyl-1H-indazol-6-amine

HRID 68677Notes

Reaction equation

HRID 68677 reaction equation
[CH3:1][S:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:4]=1>C(OCC)(=O)C.[C].[Pd]>[CH3:1][S:2][C:3]1[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[N:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:4]=1

Participants

4

Reactant 1

HCID 674475223-(methylthio)-6-nitro-1-phenyl-1H-indazole

Product 1

HCID 498399773-(methylthio)-1-phenyl-1H-indazol-6-amine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 100-mL round-bottom flask was purged, flushed and maintained with a hydrogen atmosphere, then, was added a solution of 3-(methylthio)-6-nitro-1-phenyl-1H-indazole (3.5 g, 12.28 mmol, 1.00 equiv) in ethyl acetate (30 mL), Palladium carbon (2.2 g), bubbled with H2 (gas). The resulting solution was stirred for 48 min at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum to yield 3-(methylthio)-1-phenyl-1H-indazol-6-amine as brown oil. MS: 256 (MH+)

Workup

  1. customA 100-mL round-bottom flask was purged
  2. customflushed
  3. temperaturemaintained with a hydrogen atmosphere
  4. custombubbled with H2 (gas)
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-6674f5b0ea9d4893ac7410c13786772c
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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