Hydrochloric Acid → 1-Phenyl-1H-indazol-4-amine hydrochloride

HRID 418768Notes

Reaction equation

HRID 418768 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O.[ClH:19]>CCOC(C)=O.CCOCC.O1CCOCC1.[Pd]>[ClH:19].[C:13]1([N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=3[CH:6]=[N:7]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 249381804-Nitro-1-phenyl-1H-indazole2×

Product 1

HCID 666484521-Phenyl-1H-indazol-4-amine hydrochloride

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Nitro-1-phenyl-1H-indazole (Intermediate 7) was dissolved in EtOAc (200 mL) then 10% Pd/C (500 mg) was added and the mixture was stirred under a hydrogen atmosphere for 2 hours. Filtration through Celite and concentration of the filtrate gave a yellow oil which was dissolved in ether (100 mL). A solution of 4N HCl in dioxan (10 mL) was added slowly resulting in a yellow precipitate which was filtered off to give the title compound as a yellow solid (2.5 g).

Workup

  1. filtrationFiltration through Celite and concentration of the filtrate
  2. customgave a yellow oil which
  3. customresulting in a yellow precipitate which
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-89ee22007a714f2bbacccbe260cd008e
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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