Hydrochloric Acid → 6-(Hydroxymethyl)pyridine-3-carboxylic acid

HRID 2242219Notes

Reaction equation

HRID 2242219 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[N:6][CH:5]=1.Cl>[OH-].[Na+].CO>[OH:11][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:12])=[O:2])=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 7894146-Hydroxymethyl-nicotinic acid methyl ester

Product 1

HCID 147221306-(Hydroxymethyl)pyridine-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 6-hydroxymethyl-nicotinic acid methyl ester (0.400 g, 2.38 mmol) in 1.0 N NaOH (25.0 mL) and methanol (10.0 mL) was heated at 80° C. for 1 hour. The reaction mixture was cooled to room temperature and the pH was adjusted to 7.0 with 1.0 N HCl. The reaction mixture was concentrated in vacuo and the resulting salt was slurried in DMF and filtered to provide the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-59423fface8b427fb41c791457caea82
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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