Hydrochloric Acid → 3-(3-Pyridyl)-4-amino-5-isothiazolecarboxylic acid

HRID 463888Notes

Reaction equation

HRID 463888 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:11]([NH2:12])=[C:10]([C:13]([O:15]C)=[O:14])[S:9][N:8]=2)[CH:2]=1.C(O)C.[OH-].[Na+].Cl>O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:11]([NH2:12])=[C:10]([C:13]([OH:15])=[O:14])[S:9][N:8]=2)[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 13073257Methyl 3-(3-pyridyl)-4-amino-5-isothiazolecarboxylate

Product 1

HCID 130732583-(3-Pyridyl)-4-amino-5-isothiazolecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.8 g. of methyl 3-(3-pyridyl)-4-amino-5-isothiazolecarboxylate in 20 ml. of ethanol and 20 ml. of water containing three pellets of sodium hydroxide was heated at reflux for ninety minutes. The reaction mixture was then added to 50 ml. of ice water, and the aqueous mixture was acidified by the addition of 1N aqueous hydrochloric acid. The solid precipitate was collected by filtration and recrystallized from acetic acid and water to provide 3-(3-pyridyl)-4-amino-5-isothiazolecarboxylic acid. M.P. 235°-236° C.

Workup

  1. temperatureat reflux for ninety minutes
  2. additionThe reaction mixture was then added to 50 ml
  3. filtrationThe solid precipitate was collected by filtration
  4. customrecrystallized from acetic acid and water

Sources & evidence

ORD record
ord-4ad0183e44ed4d2fb9ec248d62165e0e
Source dataset
uspto-grants-1985_10
Patent number
US04544752

Reaction notes

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