Diethyl Sulfate → HCID 15754480, compound

HRID 1030012Notes

Reaction equation

HRID 1030012 reaction equation
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][N:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[N+:18]([O-:20])=[O:19])[C:3]1=2.S(OCC)(O[CH2:25][CH3:26])(=O)=O>[OH-].[Na+]>[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[N:6]([CH2:25][CH3:26])[N:5]=[C:4]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[N+:18]([O-:20])=[O:19])[C:3]1=2

Participants

4

Reactant 2

HCID 6163Diethyl SulfateHCID 15754485HCID 15754485, compound

Product 1

HCID 15754480HCID 15754480, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.08 g (7.13 mmol) of 4,5,6,7-tetrahydro-4-oxo-3-(4-chloro-2-nitrophenyl)-1H-indazole are dissolved in 80 ml of 10% aqueous sodium hydroxide solution, insolubles are filtered off, and 1.2 g (7.8 mmol) of diethyl sulfate are then added to the solution. Stirring is subsequently continued for 1.5 hours at room temperature and for 1 hour at 0° C., during which process a precipitate starts to separate out after as early as approx. 10 minutes. When the reaction is complete, the precipitate is filtered off with suction and chromatographed on silica gel using ethyl acetate/dichloromethane (1:2). The fraction of Rf =0.72 contains 0.34 g (15.3% of theory) of the desired product of the formula ##STR7## and of melting point 184° C.

Workup

  1. filtrationinsolubles are filtered off
  2. customto separate out after as early as approx. 10 minutes
  3. filtrationthe precipitate is filtered off with suction
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-79f1724298ea40169184d1f0e4fcf92f
Source dataset
uspto-grants-1992_04
Patent number
US05104442

Reaction notes

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