Sodium Hydroxide → HCID 21942438, compound

HRID 2216771Notes

Reaction equation

HRID 2216771 reaction equation
C[O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[C:6]([F:16])[CH:5]=1.[OH-].[Na+]>CO>[F:16][C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=1)[C:3]([OH:17])=[O:2]

Participants

4

Procedure

In a 100 ml round bottom flask equipped with stir bar added Methyl-3-fluoro-5-(3-pyridyl)benzoate (0.92 g, 3.93 mmol), methanol (10 ml) and sodium hydroxide (5.89 ml, 5.89 mmol, 1N aqueous). Stirred the resulting mixture at 50° C. for 2 h. The reaction mixture was cooled to room temperature, concentrated in-vacuo and the residue was dissolved in methanol (20 ml). To this mixture added hydrochloric acid (1N diethyl ether) dropwise and stirred at room temperature for 10 min. The reaction mixture was concentrated in-vacuo and the residue was triturated with diethyl ether to provide the crude hydrochloride salt of title compound (1.00 g) as an off white solid.

Workup

  1. customIn a 100 ml round bottom flask equipped
  2. stirringStirred the resulting mixture at 50° C. for 2 h
  3. concentrationconcentrated in-vacuo
  4. dissolutionthe residue was dissolved in methanol (20 ml)
  5. additionTo this mixture added hydrochloric acid (1N diethyl ether) dropwise
  6. stirringstirred at room temperature for 10 min
  7. concentrationThe reaction mixture was concentrated in-vacuo
  8. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-36782e45cb50431e80eb316b1e128bda
Source dataset
uspto-grants-2006_09
Patent number
US07112595B2

Reaction notes

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