Hydrazine hydrate (1:1) → 6-(2-Chlorophenyl)-3-methoxymethyl-4,5,6,7-tetrahydroindazol-4-one

HRID 1700685Notes

Reaction equation

HRID 1700685 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=O)[C:11](=[C:15](O)[CH2:16][O:17][CH3:18])[C:10](=[O:20])[CH2:9]1.O.[NH2:22][NH2:23]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12]2[NH:23][N:22]=[C:15]([CH2:16][O:17][CH3:18])[C:11]=2[C:10](=[O:20])[CH2:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 183177735-(2-Chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dione

Product 1

HCID 183176226-(2-Chlorophenyl)-3-methoxymethyl-4,5,6,7-tetrahydroindazol-4-oneYield 25.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(2-chlorophenyl)-2-(1-hydroxy-2-methoxyethylidene)cyclohexane-1,3-dione (0.4 g) and hydrazine hydrate (0.072 g) in ethanol (15 ml) was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography to give 6-(2-chlorophenyl)-3-methoxymethyl-4,5,6,7-tetrahydroindazol-4-one (0.1 g) as oil.

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-f8d05efff96d436ea72f491733f4d60b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…