Water → 6-(Methyloxy)-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one

HRID 657086Notes

Reaction equation

HRID 657086 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N+:10]([O-])=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH:14]=[CH2:15])[C:6]=2[CH:16]=1.[CH3:17][O-:18].[Na+].O>CO>[CH3:17][O:18][C:2]1[CH:3]=[CH:4][C:5]2[N:10]=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH:14]=[CH2:15])[C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 144230516-Chloro-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one 1-oxide

Product 1

HCID 688207086-(Methyloxy)-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-chloro-4-(2-propen-1-yl)-1,2,4-benzotriazin-3(4H)-one 1-oxide (see Example 60(c) for a preparation) (420 mg, 1.77 mmol) in MeOH (10 ml) was added sodium methoxide solution (25% w/v, 8.84 mmol, 1.9 ml) and then the reaction was stirred at rt for 2 h. The reaction was then treated with water (100 ml) and extracted with DCM (2×100 ml). The combined organic phases were dried, evaporated and the crude residue purified by chromatography on silica gel using a 0-5% MeOH/DCM gradient, followed by trituration with diethyl ether (50 ml) to provide the desired compound as a yellow foam (205 mg, 53%).

Workup

  1. extractionextracted with DCM (2×100 ml)
  2. customThe combined organic phases were dried
  3. customevaporated
  4. customthe crude residue purified by chromatography on silica gel using a 0-5% MeOH/DCM gradient

Sources & evidence

ORD record
ord-9f6a12e8fd0740658f59e9d88e83cbe0
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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