Sodium Hydroxide → HCID 67981155, compound

HRID 1520013Notes

Reaction equation

HRID 1520013 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH:14]=2)=[N:2]1.[OH-].[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[C:17]([O:25][CH3:26])[CH:16]=3)[CH:14]=2)=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67981370HCID 67981370, compound

Product 1

HCID 67981155HCID 67981155, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]-2-methoxybenzoate (363 mg; 1.04 mmol; 1.0 eq.) suspended in MeOH (8 mL) was treated with sodium hydroxide (8.3 mL, 1N; 8.3 mmol; 8.0 eq.) and stirred at RT until all solid was dissolved (3 h). MeOH was removed under reduced pressure, the resulting solution was made acidic by addition of HCl 1N and extracted with DCM (3 times). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a beige solid (249 mg, 71%). MS (ESI+): 336.1, MS (ESI−): 334.2.

Workup

  1. dissolutionwas dissolved (3 h)
  2. customMeOH was removed under reduced pressure
  3. additionthe resulting solution was made acidic by addition of HCl 1N
  4. extractionextracted with DCM (3 times)
  5. washCombined organic phases were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-cb2b37af073a462780de5358c8ae7643
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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