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

HRID 1297586Notes

Reaction equation

HRID 1297586 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.[OH-].[Li+]>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 95.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzo[2,1,3]oxadiazol-5-yloxy)-nicotinic acid ethyl ester (2.2 g) in tetrahydrofuran (75 mL) was treated with 1M aqueous lithium hydroxide (23.1 mL) at ambient temperature for 16 h. The solution was concentrated in vacuo to remove the tetrahydrofuran, and then acidified with 1N hydrochloric acid. The resulting precipitate was filtered and dried to give the title compound (1.90 g).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto remove the tetrahydrofuran
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-56eb0954c9464447ad4884db67a91c1c
Source dataset
uspto-grants-2007_07
Patent number
US07250518B2

Reaction notes

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