Ammonium formate → HCID 178434350, compound

HRID 645676Notes

Reaction equation

HRID 645676 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[NH:4][N:3]=1.C([O-])=O.[NH4+]>C(O)C.O.CCOC(C)=O.[Fe]>[NH2:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([CH3:1])=[N:3][NH:4]2)=[CH:9][CH:8]=1

Participants

8

Reactant 2

HCID 2723923Ammonium formateHCID 109210543-Methyl-6-nitro-1H-indazole

Product 1

HCID 178434350HCID 178434350, compoundYield 81.9%

Reagents, catalysts & solvents 5

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 23925IronSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-methyl-6-nitroindazole (0.4 g, 2.24 mmol) in ethanol (EtOH) (10 mL) and H2O (5 mL) was added Iron (0.63 g, 11.22 mmol) and ammonium formate (1.4 g, 22.4 mmol). After heating at 90° C. for 2 h, the mixture was diluted with EtOAc, excess iron was removed by filtration, and the filtrate was washed sequentially with water, sat. NaHCO3, and brine, before it was dried and concentrated to give 6-amino-3-methylindazole (0.27 g).

Workup

  1. customwas removed by filtration
  2. washthe filtrate was washed sequentially with water, sat. NaHCO3, and brine, before it
  3. customwas dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-058c1ce47b934e9a91e55d29872ad8b1
Source dataset
uspto-grants-2010_04
Patent number
US07705004B2

Reaction notes

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