Hydrochloric Acid → (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetic acid

HRID 1821434Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([O:20]C)=[O:19])=[C:14]([O:24][CH3:25])[C:13]=2[N+:26]([O-:28])=[O:27])=[N:2]1.[OH-].[Na+].Cl>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:23]=[CH:22][C:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])=[C:14]([O:24][CH3:25])[C:13]=2[N+:26]([O-:28])=[O:27])=[N:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetate obtained in Step 2 in methanol (20 mL) was added with 2 mol/L aqueous sodium hydroxide solution (10 mL) and stirred at 60° C. for 1 hour. To the reaction mixture under ice-cooling, 2 mol/L hydrochloric acid was added to neutralize the mixture. The precipitated solid was collected by filtration to obtain (E)-{4-[2-(1H-indazol-3-yl)vinyl]-2-methoxy-3-nitrophenoxy}acetic acid (1.9 g, 100%).

Workup

temperatureTo the reaction mixture under ice-cooling
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-e85f4a63183042278d4e645fda456139
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605272B2

Reaction notes

Loading…