Hydrochloric Acid → HCID 58408400, compound

HRID 1948562Notes

Reaction equation

HRID 1948562 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([CH3:23])[CH:22]=3)=[CH:13][C:8]=2[C:9]([O:11]C)=[O:10])[CH:4]=[N:3]1.[OH-].[Li+].Cl>C(O)(C)C.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:16]=[CH:15][C:14]([C:17]3[CH:18]=[N:19][CH:20]=[C:21]([CH3:23])[CH:22]=3)=[CH:13][C:8]=2[C:9]([OH:11])=[O:10])[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58408406HCID 58408406, compound

Product 1

HCID 58408400HCID 58408400, compound

Reagents, catalysts & solvents 1

HCID 21889133Propan-2-ol--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a mixture of methyl 2-(1-methyl-1H-pyrazol-4-yl)-5-(5-methylpyridin-3-yl)benzoate (2-4, 0.216 g, 0.703 mmol, 1.0 equiv) in isopropanol/water (3:1, 4 mL) was added 1M lithium hydroxide solution (0.773 mL, 0.773 mmol, 1.1 equiv) and the reaction was heated to 80° C. for 15 minutes in the microwave. The reaction mixture was cooled and the pH was adjusted to ˜7 by the addition of 1N HCl. The reaction mixture was concentrated and the solids azeotroped from toluene to afford the product as a solid. ESI+ MS [M+H]+ C12H15N3O2: 308.02 found, 308.36 required.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationThe reaction mixture was concentrated
  3. customthe solids azeotroped from toluene

Sources & evidence

ORD record
ord-7bcb3dea0e8142b8bc64c77b45c89167
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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