Hydrochloric Acid → HCID 18398665, compound

HRID 2259496Notes

Reaction equation

HRID 2259496 reaction equation
Cl.[S:2]1[C:10]2[C:5](=[N:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH3:14]O>>[S:2]1[C:10]2[C:5](=[N:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12210216Thieno[3,2-b]pyridine-5-carboxylic acid

Product 1

HCID 18398665HCID 18398665, compoundYield 70%

Procedure

To a solution of HCl (10%) in MeOH (10 mL) was added thieno[3,2-b]pyridine-5-carboxylic acid (1.0 g, 5.6 mmol, from Step 2, Example 1) and the mixture heated to reflux for 2 hr. After cooling to r.t., half the solvent was removed by evaporation and the remainder was partitioned between EtOAc and H2O. Solid NaHCO3 was added until the system remained basic. Separation, drying, and evaporation of the organic layer afforded 0.75 g (70%) of methyl thieno[3,2-b]pyridine-5-carboxylate.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 2 hr
  3. customhalf the solvent was removed by evaporation
  4. customthe remainder was partitioned between EtOAc and H2O
  5. additionSolid NaHCO3 was added until the system
  6. customSeparation
  7. customdrying
  8. customevaporation of the organic layer

Sources & evidence

ORD record
ord-dd3464fd6aef4c03888ce3d35671013e
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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