5-methyl-6-nitro-1H-indazole → 5-methyl-1H-indazol-6-amine

HRID 223280Notes

Reaction equation

HRID 223280 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[NH:7][N:6]=[CH:5]2>C(O)C.O.N>[NH2:11][C:10]1[CH:9]=[C:8]2[C:4]([CH:5]=[N:6][NH:7]2)=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 126378375-methyl-6-nitro-1H-indazole2×

Product 1

HCID 126378415-methyl-1H-indazol-6-amineYield 72.2%

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

8 g (45.2 mmol) of 5-methyl-6-nitro-indazole (formula 51), obtained according to E. Noelting, Ber. Dtsch. Chem. Ges. 37 (1904) 2556, are dissolved in 640 ml of 50% aqueous ethanol. A mixture of 80 g of ferrous sulphate in 400 ml of water and 80 ml of aqueous ammonia were added. The reaction mixture was refluxed for 20 hours and filtered while still hot. Removal of the ethanol and purification of the precipitated product with charcoal yielded 4.80 g (72%) of the target compound, m.p. 241°-242° C.

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for 20 hours
  3. filtrationfiltered while still hot
  4. customRemoval of the ethanol and purification of the precipitated product with charcoal

Sources & evidence

ORD record
ord-fb3ea4d420e54dd1a56ed33b0f20ad0c
Source dataset
uspto-grants-1982_10
Patent number
US04352931

Reaction notes

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