Hydrochloric Acid → 2,3-Dimethyl-2H-indazol-6-amine

HRID 1801849Notes

Reaction equation

HRID 1801849 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([N+:12]([O-])=O)[CH:7]=[CH:8]2)=[N:3]1.[Sn](Cl)(Cl)(Cl)Cl.Cl.CCOCC>COCCOCCOC>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([NH2:12])[CH:7]=[CH:8]2)=[N:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3283Diethyl EtherHCID 24287Tin tetrachlorideHCID 104651492,3-Dimethyl-6-nitro-2H-indazole

Product 1

HCID 115428272,3-Dimethyl-2H-indazol-6-amine

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
0 °C

Procedure

2,3-dimethyl-6-nitro-2H-indazole (0.48 g, 2.5 mmol, 1 equiv) was dissolved in 2-methoxyethylether (4.3 ml) with heating then cooled down to 0° C. Tin chloride (1.6 g, 7.1 mmol, 2.8 equiv) was added under nitrogen. Concentrated HCl (3.2 ml) was added dropwise keeping the temperature below 5° C. When all the HCl was added, the reaction was allowed to warm up to room temperature and stirred for 45 min. Ether (14 ml) was added and a precipitate was collected too yield the desired product as an hydrochloride salt (0.35 g, 86.8%).

Workup

  1. temperaturewith heating
  2. customthe temperature below 5° C
  3. temperatureto warm up to room temperature
  4. customa precipitate was collected too

Sources & evidence

ORD record
ord-543d41cbf7d54f30acf806f768292844
Source dataset
uspto-grants-2013_01
Patent number
US08349861B2

Reaction notes

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