Sodium Hydroxide → 6-Carboxy-1-(2,4-dichlorobenzyl)-3-methyl-1H-indazole

HRID 1072848Notes

Reaction equation

HRID 1072848 reaction equation
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[C:7]([CH3:18])=[N:6]1.[OH-].[Na+]>C(O)C>[C:14]([C:11]1[CH:12]=[C:13]2[C:8]([C:7]([CH3:18])=[N:6][N:5]2[CH2:4][C:3]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=2[Cl:1])=[CH:9][CH:10]=1)([OH:16])=[O:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22388505HCID 22388505, compound

Product 1

HCID 223878386-Carboxy-1-(2,4-dichlorobenzyl)-3-methyl-1H-indazoleYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

1-(2,4-Dichlorobenzyl)-6-(methoxycarbonyl)-3-methyl-1H-indazole (0.2 g, 0.57 mmol) was suspended in ethanol (10 ml), and a 1M aqueous sodium hydroxide solution (2 ml) was added. The mixture was stirred under heating at 90° C. for 40 min. After the starting compound disappeared, the ethanol was distilled away under reduced pressure. The residue was acidified with 1N hydrochloric acid (3 ml) and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure to give the objective compound (0.19 g, 99%) as colorless crystals.

Workup

  1. distillationthe ethanol was distilled away under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e2b3705d5b07466ca0039ebf6afbba5e
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

Loading…