Reaction #41184

Reaction equation

hydrazinecarboxylic acid tert-butyl ester

toluene

potassium hydroxide

1-bromo-3-methoxypropane

→

N′-isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester

Yield 98.0%

Conditions

Workup

1. 1
   TemperatureThe solution was then heated to 80° C. for 3 h
2. 2
   TemperatureThe solution was cooled to room temperature
3. 3
   Washwashed with water (3×150 mL) until the water layer
4. 4
   DryingThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo

Procedure

To a solution of hydrazinecarboxylic acid tert-butyl ester (4.67 g, 27.16 mmol) in toluene (90 mL) was added pulverized potassium hydroxide (1.98 g, 35.3 mmol) and tetrabutylammonium hydrogensulfate (904 mg, 2.72 mmol). The solution was heated to 50° C. in a preheated oil bath and 1-bromo-3-methoxypropane (3.67 mL, 32.6 mmol) was added drop-wise over 45 minutes. The solution was then heated to 80° C. for 3 h. The solution was cooled to room temperature and washed with water (3×150 mL) until the water layer was neutral. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide N′-isopropylidene-N-(3-methoxypropyl)-hydrazinecarboxylic acid tert-butyl ester as a viscous oil (6.49 g, 98%), which was used without further purification. Mass spectrum: m/z: 245.4 (M+1).

Source