Hydrochloric Acid → Thieno[2,3-b]quinoline-4-carboxylic acid

HRID 641139Notes

Reaction equation

HRID 641139 reaction equation
C[O:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]2[S:15][CH:16]=[CH:17][C:6]=12)=[O:4].[OH-].[Na+].Cl>C(O)C>[S:15]1[C:7]2=[N:8][C:9]3[C:14]([C:5]([C:3]([OH:4])=[O:2])=[C:6]2[CH:17]=[CH:16]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12294104Thieno[2,3-b]quinoline-4-carboxylic acid, methyl ester

Product 1

HCID 12294105Thieno[2,3-b]quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g (4.1 mmol) methyl-thieno[2,3-b]quinoline-4-carboxylate 14, 12 ml ethanol and 60 mL 1N NaOH were mixed and heated at reflux for 75 minutes. After cooling the green solution was acidified with 4N HCl to pH ˜1-2, whereupon a solid precipitated. Then the reaction mixture was extracted with 200 mL diethylether. The organic layer was separated and extracted now with 150 mL of a sodium bicarbonate solution (5%), which was acidified another time with 4N HCl to give the product 15 as a crystalline solid. The precipitate was filtered off and dried under vacuum to give 760 mg of 15.

Workup

  1. temperatureheated
  2. temperatureat reflux for 75 minutes
  3. temperatureAfter cooling the green solution
  4. customprecipitated
  5. extractionThen the reaction mixture was extracted with 200 mL diethylether
  6. customThe organic layer was separated
  7. extractionextracted now with 150 mL of a sodium bicarbonate solution (5%), which

Sources & evidence

ORD record
ord-015a3cdfa93d46c7b9ae7ce442dd1c18
Source dataset
uspto-grants-2010_04
Patent number
US07695980B2

Reaction notes

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