Hydrochloric Acid → 2-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid

HRID 899389Notes

Reaction equation

HRID 899389 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][S:17][N:18]=[C:14]2[CH:13]=1)C.Cl>O1CCCC1.[Li+].[OH-].O>[N:16]1[S: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

6

Reactant 2

HCID 313Hydrochloric AcidHCID 235293462-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl ester

Product 1

HCID 226101592-(Benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acidYield 23.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3939Lithium HydroxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzo[2,1,3]thiadiazol-5-yloxy)-nicotinic acid ethyl ester (0.74 g, 2.5 mmol) in tetrahydrofuran (2.78 ml) and 1 M LiOH (2.7 ml) was stirred over night. The mixture was diluted with water and then acidified to pH 1 with 2 N hydrochloric acid, and thereafter filtered to give a pale yellow solid (160 mg).

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-38ce14892705467aa6be3030e7cf324f
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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