Formic Acid → Thiazolo[4,5-c]quinoline

HRID 1199978Notes

Reaction equation

HRID 1199978 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[SH:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH:13](O)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH-].[Na+]>O.Cl>[S:12]1[C:11]2[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:4]=[CH:3][C:2]=2[N:1]=[CH:13]1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 656671Sodium PyrosulfiteHCID 1785079903-Aminoquinoline-4-thiol

Product 1

HCID 3066778Thiazolo[4,5-c]quinolineYield 80%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 17.62 g (0.1 mole) of 3-amino-4-mercapto-quinoline, 150 ml of 100% formic acid and 1.5 g of sodium pyrosulfite is refluxed for 3 hours. The reaction mixture is cooled, diluted with a mixture of 800 ml of water and 40 ml of concentrated hydrochloric acid, made alkaline to pH 10 by adding a sodium hydroxide solution and extracted three times with 200 ml of benzene each. The benzene solution is evaporated. Thus 15.0 g of thiazolo[4,5-c]quinoline are obtained, m.p.: 114°-116° C., yield 80%.

Workup

  1. temperatureis refluxed for 3 hours
  2. temperatureThe reaction mixture is cooled
  3. extractionextracted three times with 200 ml of benzene each
  4. customThe benzene solution is evaporated

Sources & evidence

ORD record
ord-b77ffacd016f4f97be2a8a9d57b06ba6
Source dataset
uspto-grants-1990_02
Patent number
US04904669

Reaction notes

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