Sodium Hydroxide → 2-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylic Acid

HRID 840309Notes

Reaction equation

HRID 840309 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21]CCC)=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[OH-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 98219072-[N-(5-Bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylic Acid

Product 1

HCID 226225362-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylic AcidYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution of methyl 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylate (see reference example 1) (10.2 g, 0.55 mmol) in THF (3 ml) and methanol (5 ml) was treated with 1N aqueous sodium hydroxide solution (2.7 ml) and was heated to 40° C. for 24 hours. The solvents were evaporated at reduced pressure, the residue treated with 1N acetic acid (2.7 ml) and the precipitate filtered, washed with water and air dried to give the title compound (0.17 g, 92%).

Workup

  1. customThe solvents were evaporated at reduced pressure
  2. additionthe residue treated with 1N acetic acid (2.7 ml)
  3. filtrationthe precipitate filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-1ee2e6686cbb43ca982c4bbf11ac9cfc
Source dataset
uspto-grants-2002_04
Patent number
US06365603B1

Reaction notes

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