Sodium Hydroxide → HCID 58425463, compound

HRID 1481513Notes

Reaction equation

HRID 1481513 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:17])[N:8]=[C:9]([C:12]([CH3:16])([CH3:15])[CH2:13][F:14])[C:10]=1[Cl:11])=[O:5])C.[OH-].[Na+]>CO>[Cl:11][C:10]1[C:9]([C:12]([CH3:16])([CH3:15])[CH2:13][F:14])=[N:8][N:7]([CH3:17])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67409996HCID 67409996, compound

Product 1

HCID 58425463HCID 58425463, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-5-(2-fluoro-1,1-dimethyl-ethyl)-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester (738 mg, 2.81 mmol, prepared as described in the previous step) was dissolved in MeOH (3 mL) and 2 M NaOH (1.83 mL, 3.65 mmol) was added. The resulting mixture was stirred at room temperature for 18 h and then the solvent was removed under reduced pressure. The resulting residue was dissolved in H2O (10 mL) and then acidified to pH ˜2 with concentrated HCl. The product oiled out of solution and solidified on standing. The solid was isolated by filtration, washed with H2O (2×20 mL), and dried under high vacuum to yield 4-Chloro-5-(2-fluoro-1,1-dimethyl-ethyl)-2-methyl-2H-pyrazole-3-carboxylic acid. 1H-NMR (400 MHz, DMSO-d6) δ: 13.89 (br. s., 1H), 4.56 (d, J=48 Hz, 2H), 4.00 (s, 3H), 1.35 (d, J=1.2 Hz, 6H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe resulting residue was dissolved in H2O (10 mL)
  3. customThe solid was isolated by filtration
  4. washwashed with H2O (2×20 mL)
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-0dca70ce3bcd4d0c8a8ae5abd31b3331
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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