Sodium Hydroxide → Thieno[3,2-b]pyridin-6-amine

HRID 569070Notes

Reaction equation

HRID 569070 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[S:13][CH:12]=[CH:11][C:8]2=[N:9][CH:10]=1)(=O)C.[OH-].[Na+]>C(O)C.Cl.O>[NH2:4][C:5]1[CH:6]=[C:7]2[S:13][CH:12]=[CH:11][C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 20148566HCID 20148566, compound

Product 1

HCID 20148553Thieno[3,2-b]pyridin-6-amineYield 76%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 6-acetamidothieno[3,2-b]pyridine (2.29 g, 12 mmol) in ethanol (35 ml) and concentrated hydrochloric acid (15 ml) was warmed at 80° C. for two hours. This mixture was diluted with water and made basic by the addition of sodium hydroxide solution. The product was extracted into methylene chloride, dried over anhydrous sodium sulfate and then filtered through a pad of charcoal and the solvent was evaporated to give pure product (1.36 g, 76% yield), m.p. 121°-123° C.

Workup

  1. extractionThe product was extracted into methylene chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered through a pad of charcoal
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f3afd21ef36f475a979248a61ce74807
Source dataset
uspto-grants-1988_03
Patent number
US04731368

Reaction notes

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