Lithium Hydroxide → 5-Methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoic acid

HRID 60892Notes

Reaction equation

HRID 60892 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[Li+].[OH-]>CO.O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117727848Methyl 5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoate

Product 1

HCID 811115005-Methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

Methyl 5-methyl-2-(1-methyl-1H-pyrazol-4-yl)benzoate (˜1 g, ˜4.41 mmol) was dissolved in MeOH/H2O (4:1, 50 mL) and then LiOH (0.36 g, 15 mmol) was added. The mixture was heated at reflux for 2 h at 100° C. The analytical HPLC indicated the starting material was consumed, the mixture was cooled to 0° C. and 2 M HCl solution was added bring the pH ˜4. MeOH was removed in vacuo and the acid was precipitated. The acid was collected by filtration and dried in vacuo and used without further purification. ESI-MS (m/z): 217 [M+1]+. 1H NMR (300 MHz, DMSO-d6) δ 12.87 (br s, 1H), 7.82 (s, 1H), 7.51 (s, 1H), 7.39-7.27 (m, 3H), 3.85 (s, 3H), 2.32 (s, 3H).

Workup

  1. temperatureThe mixture was heated
  2. customwas consumed
  3. temperaturethe mixture was cooled to 0° C.
  4. addition2 M HCl solution was added
  5. customMeOH was removed in vacuo
  6. customthe acid was precipitated
  7. filtrationThe acid was collected by filtration
  8. customdried in vacuo
  9. customused without further purification

Sources & evidence

ORD record
ord-0f7284668628441a8797a09f21a1d0f9
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Reaction notes

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