Hydrochloric Acid → 5-(Pyridin-2-yl)-2(1H)-pyridone

HRID 229712Notes

Reaction equation

HRID 229712 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][N:4]=1.Cl>>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3](=[O:2])[NH:4][CH:5]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 108993656'-Methoxy-2,3'-bipyridyl

Product 1

HCID 102412575-(Pyridin-2-yl)-2(1H)-pyridoneYield 66%

Procedure

A mixture of 2-methoxy-5-pyridin-2-yl-pyridine (550 g) and a 4 mol/L aquesous solution of hydrochloric acid (2.4 L) was heated under reflux for 3 hours. After cooling the reaction solution, and washed with tert-butylmethyl ether (2.2 L). To the aqueous layer was added 8 mol/L aqueous solution of sodium hydroxide (1.1 L) under cooling with ice-water, and then the mixture was washed twice with tert-butylmethyl ether (2.2 L). Then, it was adjusted to pH 8 with concentrated hydrochloric acid (310 ml) and 8 mol/L aqueous solution of sodium hydroxide (100 ml), followed by partitioning between 1-butanol (4.5 L) and brine (1.8 L). The aqueous layer was extracted again with 1-butanol (4.5 L), and the combined organic layer was evaporated at 45-50° C. To the resulting residue was added tert-butylmethyl ether (2.2 L), to give crystals. The resulting crystals were collected by filtration under reduced pressure and air-dried at 60° C. Then, water (1.6 L) was added thereto to dissolve under heating. Then the mixture was water-cooled, and recrystallized. The resulting crystals were collected by filtration under reduced pressure and air-dried at 60° C., to give 188 g (66%) of the title compound as grayish white crystals.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling the reaction solution
  3. washwashed with tert-butylmethyl ether (2.2 L)
  4. additionTo the aqueous layer was added 8 mol/L aqueous solution of sodium hydroxide (1.1 L)
  5. temperatureunder cooling with ice-water
  6. washthe mixture was washed twice with tert-butylmethyl ether (2.2 L)
  7. customby partitioning between 1-butanol (4.5 L) and brine (1.8 L)
  8. extractionThe aqueous layer was extracted again with 1-butanol (4.5 L)
  9. customthe combined organic layer was evaporated at 45-50° C
  10. additionTo the resulting residue was added tert-butylmethyl ether (2.2 L)
  11. customto give crystals
  12. filtrationThe resulting crystals were collected by filtration under reduced pressure
  13. customair-dried at 60° C
  14. additionThen, water (1.6 L) was added
  15. dissolutionto dissolve
  16. temperatureunder heating
  17. temperaturecooled
  18. customrecrystallized
  19. filtrationThe resulting crystals were collected by filtration under reduced pressure
  20. customair-dried at 60° C.

Sources & evidence

ORD record
ord-9d92a958994c46f0a53e208189fa8cd4
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

Loading…