Water → HCID 178487565, compound

HRID 1880391Notes

Reaction equation

HRID 1880391 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1F)=O.O.O.[NH2:15][NH2:16]>>[CH3:11][O:10][C:7]1[CH:6]=[C:5]2[C:4]([C:2]([CH3:1])=[N:15][NH:16]2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 5928212'-Fluoro-4'-methoxyacetophenone

Product 1

HCID 178487565HCID 178487565, compoundYield 19%

Procedure

A solution of 2-fluoro-4-methoxyactophenone (2.0 g, 12 mmol) in hydrazine hydrate (30 mL) was heated at reflux for two days. The mixture was cooled to room temperature, poured into water and extracted with EtOAc (3×). The organic extracts were concentrated, dissolved in a minimal amount of CH2Cl2 and filtered to afford 6-methoxy-3-methyl-1H-indazole (370 mg, 19%). The filtrate was refiltered to provide additional product (250 mg, 13%).

Workup

  1. temperatureat reflux for two days
  2. extractionextracted with EtOAc (3×)
  3. concentrationThe organic extracts were concentrated
  4. dissolutiondissolved in a minimal amount of CH2Cl2
  5. filtrationfiltered

Sources & evidence

ORD record
ord-2246ddd0160940e7ba2fec83d24e4069
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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