Bromoacetone → HCID 13900241, compound

HRID 544473Notes

Reaction equation

HRID 544473 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]>C(COC)OC.C(O)C>[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

5

Reactant 2

HCID 11715BromoacetoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

Product 1

HCID 13900241HCID 13900241, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 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 hours at room temperature and then heated at 65° with stirring for 14 hours.The solid which separates is isolated by filtration, dissolved in 800 ml absolute ethanol and heated under a reflux for 6 hours. The ethanol solvent is removed under reduced pressure and the residue treated with 138ml 6 N hydrochloric acid in 750 ml water for 0.5 hour. 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-formyl-imidazo[1,2-a]pyridine, mp 136°-139.5° C.

Workup

  1. temperatureheated at 65°
  2. stirringwith stirring for 14 hours
  3. customThe solid which separates is isolated by filtration
  4. temperatureheated under
  5. temperaturea reflux for 6 hours
  6. customThe ethanol solvent is removed under reduced pressure
  7. additionthe residue treated with 138ml 6 N hydrochloric acid in 750 ml water for 0.5 hour
  8. washThe acidic aqueous layer is washed with ether (2×300 ml)
  9. temperaturewith cooling (78 ml) 50% sodium hydroxide and 25 g sodium bicarbonate)
  10. extractionThe aqueous layer is extracted with dichloromethane
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltration
  13. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-eb2158627065455a9db7a5f6dad4c90d
Source dataset
uspto-grants-1984_05
Patent number
US04450164

Reaction notes

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