Hydrogen Bromide → 2-Pyridinecarboxylic acid, 5-((4-hydroxyphenyl)methyl)-

HRID 2420104Notes

Reaction equation

HRID 2420104 reaction equation
Br.C[O:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([OH:17])=[O:16])=[N:13][CH:14]=2)=[CH:6][CH:5]=1.[OH-].[Na+]>>[OH:3][C:4]1[CH:19]=[CH:18][C:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]([OH:17])=[O:16])=[N:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 20313036HCID 20313036, compound

Product 1

HCID 30437922-Pyridinecarboxylic acid, 5-((4-hydroxyphenyl)methyl)-Yield 70.7%

Procedure

Five milliliters of 47% hydrobromic acid were added to 1.5 g of 5-(4-methoxybenzyl)picolinic acid. The mixture was heated under reflux for three hours. After allowing to cool, the reaction mixture was adjusted to around pH 2 with 10% aqueous NaOH solution to form crystals. The crystals were collected by filtration and then recrystallized from methanol to obtain 1.0 g of 5-(4-hydroxybenzyl)-picolinic acid as crystals of a melting point of 213°~215° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for three hours
  3. temperatureto cool
  4. customto form crystals
  5. filtrationThe crystals were collected by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9ce5da2c02364c4282d60772b7bff0eb
Source dataset
uspto-grants-1978_08
Patent number
US04109000

Reaction notes

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