Hydrochloric Acid → HCID 13900241, compound

HRID 544470Notes

Reaction equation

HRID 544470 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:11][C:12](=O)[CH3:13].Cl>C(COC)OC.C(O)C.O>[CH3:13][C:12]1[N:1]=[C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][N:9]2[CH:11]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 11715BromoacetoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 13900241HCID 13900241, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-aminonicotinaldehyde (92.8 g, 0.76 mol) and bromoacetone (114.5 g, 0.84 mol) in dimethoxyethane (980 ml) is stirred for 2 hr. at room temperature and then heated at 65° with stirring for 14 hr. The solid which separates is isolated by filtration, dissolved in 800 ml absolute ethanol and heated under reflux for 6 hrs. The ethanol solvent isremoved under reduced pressure and the residue treated with 138 ml 6 N hydrochloric acid in 750 ml water for 0.5 hr. The acidic aqueous layer is washed with ether (2×300 ml) and basified with cooling (78 ml 50% sodium hydroxide and 25 g sodium bicarbonate). The aqueous layer is extracted with dichloromethane. The extracts are combined and dried over anhydrous sodium sulfate. Following filtration, the solvent is removed under reduced pressure to afford 2-methyl-8-formylimidazo[1,2-a]pyridine, mp 136°-139.5° C.

Workup

  1. stirringwith stirring for 14 hr
  2. customThe solid which separates is isolated by filtration
  3. temperatureheated
  4. temperatureunder reflux for 6 hrs
  5. washThe acidic aqueous layer is washed with ether (2×300 ml)
  6. temperaturewith cooling (78 ml 50% sodium hydroxide and 25 g sodium bicarbonate)
  7. extractionThe aqueous layer is extracted with dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltration
  10. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7cffbc95f15649e6b9e23676620e6eba
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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