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

HRID 840286Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:21]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19]C)=[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]([O:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH:21]=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

Conditions

Temperature: 40 °C

Procedure

A solution of methyl 2-[N-(5-bromo-2-propoxybenzyl)-N-ethylamino]pyridine-5-carboxylate (reference example 1) (0.12 g, 0.29 mmol) in THF (3 ml) and methanol (3 ml) was treated with aqueous sodium hydroxide (1N, 1.8 ml). The reaction was heated to 40° C. for 18 hours. The solvent was then evaporated off and the residue diluted with water (3 ml) and acidified with acetic acid (1N, 3 ml). The solid was filtered off to give the title compound (0.1 g, 88%) as a white solid.

Workup

customThe solvent was then evaporated off
additionthe residue diluted with water (3 ml)
filtrationThe solid was filtered off

Sources & evidence

ORD record: ord-c48b0cba0c254597bbf4c382b8d86fbc
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365603B1

Reaction notes

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