Sodium Hydroxide → 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 1481515Notes

Reaction equation

HRID 1481515 reaction equation
[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([O:13]C)=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([N:5]1[C:9]([CH3:10])=[C:8]([C:11]([OH:13])=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50853230Methyl 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylate

Product 1

HCID 222279031-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylate in MeOH (20 mL) was treated with 2 M aqueous NaOH solution (7.95 mL, 15.9 mmol) for 48 h at room temperature. The solvent was removed under reduced pressure and the resulting residue was dissolved in H2O (20 mL). The resulting solution was then acidified to pH-2 using 2 M HCl. The resulting precipitate was isolated by filtration, washed once with H2O (20 mL), and the solid was dried under high vacuum to yield 1-tert-Butyl-5-methyl-1H-pyrazole-4-carboxylic acid. 1H-NMR (400 MHz, d6-DMSO) δ: 12.16 (br. s., 1H), 7.67 (s, 1H), 2.69 (s, 3H), 1.59 (s, 9H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in H2O (20 mL)
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed once with H2O (20 mL)
  5. customthe solid was dried under high vacuum

Sources & evidence

ORD record
ord-af383baef1244dd5b13731f02d589b57
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

Loading…