Lithium Hydroxide → 2-(2,1,3-Benzoxadiazol-5-yloxy)nicotinic acid

HRID 899379Notes

Reaction equation

HRID 899379 reaction equation
C([O:3][C:4](=[O:21])[C:5]1[CH:10]=[CH:9][CH:8]=[N:7][C:6]=1[O:11][C:12]1[CH:20]=[CH:19][C:15]2=[N:16][O:17][N:18]=[C:14]2[CH:13]=1)C.[Li+].[OH-]>O1CCCC1>[N:16]1[O:17][N:18]=[C:14]2[CH:13]=[C:12]([O:11][C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:5]=3[C:4]([OH:21])=[O:3])[CH:20]=[CH:19][C:15]=12

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 235293452-(Benzo[2,1,3]oxadiazol-5-yloxy)-nicotinic acid ethyl ester

Product 1

HCID 226101382-(2,1,3-Benzoxadiazol-5-yloxy)nicotinic acidYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2.2 g (7.7 mmol) 2-[benzo[2,1,3]oxadiazol-5-yloxy]-nicotinic acid ethyl ester and 23.1 ml (23.1 mmol) 1M LiOH in 75 ml tetrahydrofuran was stirred overnight at room temperature. The tetrahydrofuran was evaporated in vacuo and the aqueous mixture was then acidified with 1N HCl. The resulting precipitate was filtered and dried to give 1.9 g (96%) solid.

Workup

  1. customThe tetrahydrofuran was evaporated in vacuo
  2. filtrationThe resulting precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-06df262b88274a9eb58e0928ef34f19c
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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