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

HRID 1604353Notes

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-6fcd451e6ec54d09b36a875090ad3445
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994353

Reaction notes

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