Hydrochloric Acid → HCID 22326703, compound

HRID 896294Notes

Reaction equation

HRID 896294 reaction equation
C([N:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][CH2:15][Cl:16])[CH:9]=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl>CO>[Cl:16][CH2:15][CH2:14][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH:6]=[N:5][NH:4]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22350151HCID 22350151, compound

Product 1

HCID 22326703HCID 22326703, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

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.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additiondiluted with H2O and ethyl acetate
  4. customThe phases are separated
  5. extractionthe aqueous phase is extracted with ethyl acetate
  6. washThe combined organic phases are washed with water and saturated NaCl
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-72459e4268e746c3bdd005b7f200ed50
Source dataset
uspto-grants-2005_07
Patent number
US06919354B2

Reaction notes

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