Hydrochloric Acid → HCID 86602665, compound

HRID 1445543Notes

Reaction equation

HRID 1445543 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([O:15]CC)=[O:14])=[CH:11][C:10]([O:18][CH2:19][C:20]#[CH:21])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.CO.[OH-].[Na+].Cl>O>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]([O:18][CH2:19][C:20]#[CH:21])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 86602666HCID 86602666, compound2×

Product 1

HCID 86602665HCID 86602665, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 50 mL flask containing ethyl 1-(3-chloro-2-pyridinyl)-3-(2-propynyloxy)-1H-pyrazole-5-carboxylate (i.e. the product of Step A) (0.45 g, 1.5 mmol) and 10 mL of methanol was added dropwise a mixture of 50% sodium hydroxide (0.7 g, 8.75 mmol) in water (4.0 mL). The mixture was heated to near reflux and then cooled to ambient temperature with stirring continued for 15 minutes. To this mixture was added a solution of 1 N HCl (9.0 mL) and the reaction mixture was concentrated on rotary evaporator to approximately 5 mL to precipitate a solid. The product was isolated via filtration, washed with water, and then air-dried on the filter to afford 0.31 g of the title compound as a white solid.

Workup

  1. additionwas added dropwise
  2. temperatureThe mixture was heated
  3. temperatureto near reflux
  4. concentrationthe reaction mixture was concentrated on rotary evaporator to approximately 5 mL
  5. customto precipitate a solid
  6. customThe product was isolated via filtration
  7. washwashed with water
  8. customair-dried on the
  9. filtrationfilter

Sources & evidence

ORD record
ord-1abaa9f3b04e47c7b3d1f8e8acb2414e
Source dataset
uspto-grants-2010_02
Patent number
US07666882B2

Reaction notes

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