Sodium Hydroxide → HCID 57642391, compound

HRID 2112541Notes

Reaction equation

HRID 2112541 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[C:3]=1[C:11]([O:13]CC)=[O:12].[OH-].[Na+]>O1CCCC1.O.CO>[Cl:1][C:2]1[N:6]([CH2:7][CH:8]=[CH2:9])[N:5]=[C:4]([CH3:10])[C:3]=1[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57642348HCID 57642348, compound

Product 1

HCID 57642391HCID 57642391, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 5.0 g (0.0249 mole) of ethyl 5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole-4-carboxylate (XVI) in 40 mL of tetrahydrofuran-water-methanol (3:1:1) was added 5 mL of 10 M sodium hydroxide solution. The mixture was heated at 65° C. for 4 hours and then concentrated to a smaller volume under reduced pressure. The pH was adjusted to 1-2 by the addition of hydrochloric acid. The product was collected by filtration, washed with water and dried to yield 4.7 g of 5-chloro-3-methyl-1-(2-propenyl)-1H-pyrazole-4-carboxylic acid (XVII) as a tan solid.

Workup

  1. concentrationconcentrated to a smaller volume under reduced pressure
  2. additionThe pH was adjusted to 1-2 by the addition of hydrochloric acid
  3. filtrationThe product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0d991d6597924f4980817276f0e6e2b6
Source dataset
uspto-grants-2009_04
Patent number
US07524840B2

Reaction notes

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