Reaction #2069975

Reaction equation

1-acetyl-4-(2-chloroethoxy)-indazole

hydrochloric acid

→

title product

Yield 96.9%

4-(2-Chloroethoxy)-1H-indazole

Yield 96.9%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   Concentrationconcentrated in vacuo
3. 3
   workup.ADDITIONdiluted with H2O and ethyl acetate
4. 4
   OtherThe phases are separated
5. 5
   Extractionthe aqueous phase is extracted with ethyl acetate
6. 6
   WashThe combined organic phases are washed with water and saturated NaCl
7. 7
   Dryingdried over Na2SO4
8. 8
   Concentrationconcentrated in vacuo

Procedure

A stirred solution of 1-acetyl-4-(2-chloroethoxy)-indazole (1.50 g, 6.3 mmol) in methanol is treated with hydrochloric acid (6.3 ml, 1.0 M HCl in Et2O, 6.3 mmol) at room temperature, heated at 65° C. under nitrogen for 18 hr, cooled to room temperature and concentrated in vacuo. The resultant residue is neutralized with 1N NaOH (6.0 ml) and diluted with H2O and ethyl acetate. The phases are separated and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with water and saturated NaCl, dried over Na2SO4 and concentrated in vacuo to afford the title product (1.2 g) as a yellow solid, identified by NMR and mass spectral analyses.

Source