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

HRID 336263Notes

Reaction equation

HRID 336263 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 ethyl acetate. The combined organic phase was dried over magnesium sulphate and concentrated in vacuo to afford the title compound (0.63 g, 99%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-0c635cb86ad44bf2b0fafc8b6bbdf28f
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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