Sodium Hydroxide → HCID 67958419, compound

HRID 2174664Notes

Reaction equation

HRID 2174664 reaction equation
[N:1]1[N:2]([C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([O:14]CC)=[O:13])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2.[OH-].[Na+]>O1CCCC1.CO>[N:1]1[N:2]([C:10]2[N:20]=[CH:19][CH:18]=[CH:17][C:11]=2[C:12]([OH:14])=[O:13])[CH:3]=[C:4]2[C:9]=1[CH:8]=[CH:7][CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66720187HCID 66720187, compound

Product 1

HCID 67958419HCID 67958419, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2H-indazol-2-yl)nicotinate (3.44 g, 12.87 mmol; prepared according to procedures of WO 2008/080969) in a mixture of tetrahydrofurane (THF) (50 ml) and methanol (100 ml) a 2 M aqueous solution of sodium hydroxide (20 ml) was added and stirred over night at room temperature. The mixture then was concentrated. Water (200 ml) and then a 2 N aqueous solution of hydrochloric acid (HCl) (40 ml) were added, and the immediately formed solid was filtered off under suction. Treatment of the solids with ethylacetate (50 ml) gave 2.95 g of the title compound as a white solid.

Workup

  1. additionwas added
  2. concentrationThe mixture then was concentrated
  3. additionWater (200 ml) and then a 2 N aqueous solution of hydrochloric acid (HCl) (40 ml) were added
  4. filtrationthe immediately formed solid was filtered off under suction

Sources & evidence

ORD record
ord-55f9c694f5f2437eae16fd4a389c871d
Source dataset
uspto-grants-2015_06
Patent number
US09062027B2

Reaction notes

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