Sodium Hydroxide → HCID 178524452, compound

HRID 1378917Notes

Reaction equation

HRID 1378917 reaction equation
C([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[C:11]1[CH:15]=[CH:14][NH:13][N:12]=1)C.[OH-].[Na+:18]>CO.O>[Na+:18].[NH:13]1[CH:14]=[CH:15][C:11]([C:6]2[N:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4]([O-:16])=[O:3])=[N:12]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178468988HCID 178468988, compound

Product 1

HCID 178524452HCID 178524452, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.61 g of 2-(pyrazol-3-yl)-nicotinic acid ethyl ester are dissolved in 20 ml of methanol and 0.5 g of NaOH in 5 ml of water added. After standing for 1 hr the methanol is removed under vacuum and an additional 0.07 g of NaOH added and dissolved by warming. After standing for 1 hr the mixture is diluted with H2O to 20 ml and divided into 4 aliquots of 5 ml. Each aliquot is chromatographed on Waters C18 sep. pak cartridge with 5 ml MeOH and 5 ml H2O each. The aqueous phases are combined, adjusted to pH 7.7 with HCl and freeze dried to give the title compound, m.p. 260°.

Workup

  1. customthe methanol is removed under vacuum
  2. additionan additional 0.07 g of NaOH added
  3. dissolutiondissolved
  4. temperatureby warming
  5. waitAfter standing for 1 hr
  6. additionthe mixture is diluted with H2O to 20 ml
  7. customEach aliquot is chromatographed on Waters C18 sep
  8. customdried

Sources & evidence

ORD record
ord-a79825c88e3d48a58c6ad9778265192a
Source dataset
uspto-grants-1997_09
Patent number
US05670456

Reaction notes

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