Sodium Hydroxide → HCID 13729345, compound

HRID 341543Notes

Reaction equation

HRID 341543 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.[OH-].[Na+]>CCO>[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([O:7][C:8]2[N:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66803216HCID 66803216, compound2×

Product 1

HCID 13729345HCID 13729345, compoundYield 170%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 6-[(1-methylpyrrolidin-3-yl)oxy]pyridine-3-carboxylate (Intermediate 241, 0.089 g, 0.36 mmol) was dissolved in EtOH (2 mL), 2M aq. sodium hydroxide (0.53 mL, 1.07 mmol) was added and the mixture was stirred at room temperature for 4 h. The mixture was concentrated under vacuum and the residue acidified to pH 6 by adding 2M hydrochloric acid. The mixture was then concentrated and dried under vacuum to afford the title compound as a cream solid (0.136 g), which was used directly in the next step without further purification. Method C HPLC-MS: MH+ requires m/z=223 Found: m/z=223, Rt=0.38 min (17% by ELS).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionby adding 2M hydrochloric acid
  3. concentrationThe mixture was then concentrated
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e377fdec860041de88e60345ccb97434
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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