Lithium Hydroxide → HCID 178425888, compound

HRID 1488121Notes

Reaction equation

HRID 1488121 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:18]#[N:19])[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([O:12]C)=[O:11].[Li+].[OH-]>CO.O>[Cl:1][C:2]1[N:3]=[C:4]([C:18]#[N:19])[NH:5][C:6]=1[C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:16]=1[CH3:17])[C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 178497721HCID 178497721, compound2×

Product 1

HCID 178425888HCID 178425888, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a 25-mL round-bottom flask, was placed a solution of methyl 3-(4-chloro-2-cyano-1H-imidazol-5-yl)-4-methylbenzoate (compound 234.4, 130 mg, 0.47 mmol) in methanol (4 mL). Then a solution of LiOH (45.4 mg, 1.90 mmol) in water (2 mL) was added to the reaction. The reaction mixture was stirred overnight at 30° C., then was concentrated under reduced pressure. The pH of the solution was adjusted to 3 with hydrogen chloride (1M) and was concentrated under reduced pressure. Methanol (5 mL) was added to the residue. The salt was filtered off, and the filtrate was concentrated under reduced pressure to give 150 mg (crude) of the title compound as a white solid.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. concentrationwas concentrated under reduced pressure
  3. concentrationwas concentrated under reduced pressure
  4. additionMethanol (5 mL) was added to the residue
  5. filtrationThe salt was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b289bff1287849b3aebf604cba2f5a20
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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