Water → HCID 86692494, compound

HRID 1748543Notes

Reaction equation

HRID 1748543 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:12]2[C:13]([Cl:21])=[N:14][CH:15]=[C:16]([CH:18]3[CH2:20][CH2:19]3)[CH:17]=2)[C:10]=1[CH3:11])=[O:5])C.[OH-].[Na+].O>O1CCCC1>[Cl:21][C:13]1[C:12]([N:9]2[C:10]([CH3:11])=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]2)=[CH:17][C:16]([CH:18]2[CH2:20][CH2:19]2)=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86692493HCID 86692493, compound

Product 1

HCID 86692494HCID 86692494, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-chloro-5-cyclopropylpyridin-3-yl)-5-methyl-1H-pyrazole-4-carboxylic acid ethyl ester (1.13 g) in tetrahydrofuran (30 ml) were added 4 N aqueous solution of sodium hydroxide (30 ml) and water (20 ml), and stirred at room temperature overnight. After completion of the reaction, the organic solvent was evaporated in vacuo, then water and diethyl ether were added thereto, and the aqueous layer was separated. To the aqueous layer was added concentrated hydrochloric acid under ice-cooling to adjust the layer to pH 5, the precipitated solid was collected by filtration, washed, and then dried at 60° C. under air blow to give the titled compound (922 mg) as a white solid. MS (ESI) m/z: 278 (M+H)+.

Workup

  1. customAfter completion of the reaction
  2. customthe organic solvent was evaporated in vacuo
  3. additionwater and diethyl ether were added
  4. customthe aqueous layer was separated
  5. additionTo the aqueous layer was added concentrated hydrochloric acid under ice-
  6. temperaturecooling
  7. filtrationthe precipitated solid was collected by filtration
  8. washwashed
  9. customdried at 60° C. under air blow

Sources & evidence

ORD record
ord-f903f41dc9004eeaac3b5f83984463df
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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