Lithium Hydroxide → 2-(1,4-dimethyl-1H-pyrazol-5-yl)benzoic acid

HRID 64212Notes

Reaction equation

HRID 64212 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11]C)=[O:10])=[C:5]([CH3:17])[CH:4]=[N:3]1.[Li+].[OH-]>CO>[CH3:1][N:2]1[C:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([OH:11])=[O:10])=[C:5]([CH3:17])[CH:4]=[N:3]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90416417Methyl 2-(1,4-dimethyl-1H-pyrazol-5-yl)benzoate

Product 1

HCID 826139312-(1,4-dimethyl-1H-pyrazol-5-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the title compound of Step A (680 mg, 2.95 mmol) in MeOH (15 mL) was added 4 M LiOH (4 mL). The mixture was heated at 50° C. overnight. MeOH was removed and HCl added until pH=2. White solids precipitated from the reaction mixture and the precipitate was filtered, washed with EtOAc and collected to give intermediate A-31, which was used without further purification in subsequent steps. MS (ESI) mass calcd. for C12H12N2O2, 216.1. m/z found 217.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 12.87 (s, 1H), 7.95 (dd, J=7.8, 1.5 Hz, 1H), 7.67 (td, J=7.5, 1.5 Hz, 1H), 7.59 (td, J=7.6, 1.4 Hz, 1H), 7.33 (dd, J=7.6, 1.4 Hz, 1H), 7.25 (s, 1H), 3.48 (s, 3H), 1.77 (s, 3H).

Workup

  1. customMeOH was removed
  2. additionHCl added until pH=2
  3. customWhite solids precipitated from the reaction mixture
  4. filtrationthe precipitate was filtered
  5. washwashed with EtOAc
  6. customcollected
  7. customto give intermediate A-31, which
  8. customwas used without further purification in subsequent steps

Sources & evidence

ORD record
ord-6496a0712a6c41a2be78c2a806641cb5
Source dataset
uspto-grants-2016_09
Patent number
US09447117B2

Reaction notes

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