Methanol → HCID 178524632, compound

HRID 516436Notes

Reaction equation

HRID 516436 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([OH:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:7]=1)=[O:5])C.CO>O>[OH:11][C:9]1[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 178469354HCID 178469354, compound

Product 1

HCID 178524632HCID 178524632, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 5-hydroxy-1-pyridin-2-yl-1h-pyrazole-3-carboxylic acid ethyl ester (351.6 mg, 1.5 mmol) in MeOH (5.0 mL, 120 mmol) at room temperature was added LiOH monohydrate (126.5 mg, 3.0 mmol), forming a clear solution. The solution was stirred at room temperature overnight. The solution was then concentrated. To the resulting residue was added 1N aqueous HCl to achieve pH˜2, forming a precipitate. Water (4.0 mL) was added and the resulting mixture was stirred at room temperature for 1 hour, then filtered. The solids were rinsed with water and dried under vacuum to yield the title compounds as a white solid (128 mg).

Workup

  1. customforming a clear solution
  2. concentrationThe solution was then concentrated
  3. additionTo the resulting residue was added 1N aqueous HCl
  4. customforming a precipitate
  5. stirringthe resulting mixture was stirred at room temperature for 1 hour
  6. filtrationfiltered
  7. washThe solids were rinsed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-d7ea22e8e8614a90a082084a60de0f16
Source dataset
uspto-grants-2015_08
Patent number
US09108934B2

Reaction notes

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