Hydrochloric Acid → 1-methyl-1H-indazol-5-amine

HRID 1750888Notes

Reaction equation

HRID 1750888 reaction equation
Cl.[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[CH:5]=[N:4]1>[Fe].C(O)C.O>[CH3:2][N:3]1[C:11]2[C:6](=[CH:7][C:8]([NH2:12])=[CH:9][CH:10]=2)[CH:5]=[N:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2802111-Methyl-5-nitro-1H-indazole

Product 1

HCID 27680321-methyl-1H-indazol-5-amineYield 71.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron (3.62 g, 64.7 mmol) and concentrated hydrochloric acid (0.1 mL) were added to ethanol/water (20 mL/20 mL), and refluxed for 1 hour. The mixed reaction solution was added with 1-methyl-5-nitro-1H-indazole (2.29 g, 12.9 mmol) obtained in <Step 1> above, and further refluxed for 3 hours or more. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with chloroform/2-propanol=4/1(v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol=4/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (1.35 g, 71%).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe mixed reaction solution
  3. customobtained in <Step 1> above, and
  4. temperaturefurther refluxed for 3 hours or more
  5. filtrationThe reaction mixture was filtered through a Celite pad under reduced pressure
  6. washwashed with chloroform/2-propanol=4/1(v/v)
  7. customThe filtrate obtained
  8. distillationwas distilled under reduced pressure
  9. dissolutiondissolved in chloroform/2-propanol=4/1 (v/v)
  10. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and brine
  11. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1024d3bd0fee437282badb19d04702c0
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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