Hydrochloric Acid → 3-(2-Chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylic acid

HRID 1047628Notes

Reaction equation

HRID 1047628 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]C)=[O:18])=[CH:14][CH:15]=2)[N:10]([CH:21]([CH3:23])[CH3:22])[N:9]=1.[OH-].[Na+].Cl>CO.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[N:10]([CH:21]([CH3:23])[CH3:22])[N:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66661389Methyl 3-(2-chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylate

Product 1

HCID 666615033-(2-Chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylic acidYield 97.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 3-(2-chlorophenyl)-1-isopropyl-1H-indazole-6-carboxylate (57.7 mg, 0.18 mmol) in methanol (1.1 mL) and tetrahydrofuran (0.7 mL) was added sodium hydroxide (1.0 M, 1.10 mL, 1.10 mmol). The mixture was heated to 50° C. and stirred for 18 h. The mixture was cooled to ambient temperature and 1.0 M hydrochloric acid (ca 1.1 mL) was added until pH<3. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with saturated aqueous sodium chloride (1×7 mL), dried over sodium sulfate, filtered and concentrated to give the title compound (55.0 mg): LC-MS [M+1]=315.0.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layer was washed with saturated aqueous sodium chloride (1×7 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-799fcb7e6ac447dc923579a428f528c3
Source dataset
uspto-grants-2013_10
Patent number
US08569512B2

Reaction notes

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