Sodium Hydroxide → 2-{[(2-Methoxyphenyl)methyl]amino}pyridine-3-carboxylic acid

HRID 2194519Notes

Reaction equation

HRID 2194519 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH2:16].[OH-].[Na+]>>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][NH:16][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 762582-Chloronicotinic acidHCID 812922-Methoxybenzylamine

Product 1

HCID 257062592-{[(2-Methoxyphenyl)methyl]amino}pyridine-3-carboxylic acidYield 74.5%

Procedure

7.00 g (44.2 mmol) of 2-chloronicotinic acid and 12.13 g (88.4 mmol) of 2-methoxybenzylamine were heated at 140° C. for 4 hours. The mixture was left to cool to room temperature, and then a 10% aqueous solution of sodium hydroxide was added to the reaction mixture. The resulting mixture was washed with chloroform. Concentrated hydrochloric acid was added to the aqueous phase to adjust the aqueous phase to pH 6 to 7, and a solid precipitated therefrom was separated by filtration and dried. Thus, 8.50 g (yield: 74%) of the title compound was obtained as a pale yellow powder.

Workup

  1. waitThe mixture was left
  2. washThe resulting mixture was washed with chloroform
  3. additionConcentrated hydrochloric acid was added to the aqueous phase
  4. customa solid precipitated
  5. customtherefrom was separated by filtration
  6. customdried

Sources & evidence

ORD record
ord-bf36e58826fb47e7a7c3e35c28e485b4
Source dataset
uspto-grants-2012_12
Patent number
US08334236B2

Reaction notes

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