Sodium Hydroxide → Thieno(3,2-c)pyridine

HRID 971900Notes

Reaction equation

HRID 971900 reaction equation
C([CH:4]1[N:9](N=O)[CH2:8][C:7]2[CH:12]=[CH:13][S:14][C:6]=2[CH:5]1O)(O)=O.[OH-].[Na+]>Cl>[S:14]1[C:6]2[CH:5]=[CH:4][N:9]=[CH:8][C:7]=2[CH:12]=[CH:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21312555HCID 21312555, compound

Product 1

HCID 67500Thieno(3,2-c)pyridine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 24 g of the nitroso derivative obtained in Example 2 in 200 cc 6 N hydrochlorid acid is heated at 60° C. for 2 hours. Gas is evolved, and russet fumes are formed. After cooling, the brown reaction medium is made basic with aqueous sodium hydroxide and is then extracted with methylene chloride. The organic extracts are washed with water, dried over sodium sulfate, decolorized with carbon black, filtered through talc and evaporated to dryness. Vacuum distillation of the residue gives 6.5 g (overall yield, from the starting material of the formula (IV): 43%) thieno[3,2-c]pyridine which crystallizes on cooling. M.p. <50° C.

Workup

  1. customrusset fumes are formed
  2. temperatureAfter cooling
  3. extractionis then extracted with methylene chloride
  4. washThe organic extracts are washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered through talc
  7. customevaporated to dryness
  8. distillationVacuum distillation of the residue
  9. customgives 6.5 g (overall yield
  10. customfrom the starting material of the formula (IV): 43%) thieno[3,2-c]pyridine which crystallizes
  11. temperatureon cooling

Sources & evidence

ORD record
ord-d289677145034760946363dafddf2152
Source dataset
uspto-grants-1979_07
Patent number
US04161599

Reaction notes

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