Sodium Hydroxide → 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

HRID 1476376Notes

Reaction equation

HRID 1476376 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([O:16]C)=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[OH-].[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:12])[CH3:13])[C:9]=2[CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67468514Methyl 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylate

Product 1

HCID 674688776-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-chloro-1-(1-methylethyl)-1H-indazole-4-carboxylate (0.22 g, 0.871 mmol) was dissolved in methanol (6 mL) and THF (1 mL), followed by addition of NaOH (1.451 mL, 4.35 mmol) via syringe. The contents were stirred at RT for 3 h. The volatiles were removed in vacuo, the contents diluted with water, and then slowly acidified to pH 4-5 by addition of 1M HCl (solid precipitation occurred). The contents were then extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The collected solid was dried under hi-vac for 2 h, and collected as 0.19 g (90%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.47 (d, J=6.57 Hz, 6H) 5.09 (quin, J=6.57 Hz, 1H) 7.70 (d, J=1.52 Hz, 1H) 8.25 (s, 1H) 8.40 (s, 1H), 13.54 (br. s., 1H).

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe contents diluted with water
  3. additionslowly acidified to pH 4-5 by addition of 1M HCl (solid precipitation occurred)
  4. extractionThe contents were then extracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe collected solid was dried under hi-vac for 2 h
  10. customcollected as 0.19 g (90%)

Sources & evidence

ORD record
ord-ba6a74fdf0784c158fdf7a19b822b47a
Source dataset
uspto-grants-2015_04
Patent number
US09018382B2

Reaction notes

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