Hydrochloric Acid → 6-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinic acid

HRID 219812Notes

Reaction equation

HRID 219812 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]1[C:16]([CH3:17])=[CH:15][C:12]([C:13]#N)=[CH:11][N:10]=1.[OH-:18].[K+].Cl.[OH2:21]>>[CH3:1][O:2][CH2:3][CH:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]1[C:16]([CH3:17])=[CH:15][C:12]([C:13]([OH:21])=[O:18])=[CH:11][N:10]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 675302276-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrile

Product 1

HCID 594958236-[2-(Methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinic acidYield 99%

Procedure

A mixture of 6-[2-(methoxymethyl)pyrrolidin-1-yl]-5-methylnicotinonitrile (591 mg; 2.56 mmol; 1 eq.) and potassium hydroxide (717 mg; 12.8 mmol; 5 eq.) in water (20 mL) was stirred at reflux for 16 hours. The pH was adjusted to 5-6 with HCl 1M and the aqueous layer extracted with EtOAc. The combined organic phase was dried over MgSO4 and concentrated in vacuo to afford the title compound as a white solid (0.63 g, 99%). LC/MS: 219.1 (M+H)+. HPLC (Method A): Rt 1.44 min (purity 96.6%).

Workup

  1. temperatureat reflux for 16 hours
  2. extractionthe aqueous layer extracted with EtOAc
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f99a4d4afe2d4f948e3109db12c791ec
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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