Water → 1,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-one

HRID 1068792Notes

Reaction equation

HRID 1068792 reaction equation
[H-].[Na+].Cl.[NH2:4][C:5]1[N:10]2[C:11]([C:15]([O:17]CC)=O)=[C:12]([CH3:14])[N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.O>CN(C=O)C>[CH3:14][C:12]1[N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[N:10]2[C:11]=1[C:15](=[O:17])[NH:4]3

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 21190091HCID 21190091, compound

Product 1

HCID 1358102941,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-oneYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4.8 g (120 mmol) of sodium hydride (60% dispersion in oil) in 60 ml of DMF was added 10.23 g (40 mmol) of 5-amino-3-ethoxycarbonyl-2-methylimidazo[1,2-a]pyridine.hydrochloride with small portions. The mixture was stirred for 0.5 hour, then for 0.5 hour at 100° C., which was left standing for cooling. To the reaction mixture was added 60 ml of water. The mixture was washed with chloroform, to which was added, while stirring at room temperature, conc. HCl to make the pH of the solution 8. The resulting precipitate was collected by filtration, washed with water and ether, successively to give 5.97 g of the desired compound (86.1%, pale brown solid).

Workup

  1. waitfor 0.5 hour at 100° C.
  2. waitwhich was left
  3. temperaturefor cooling
  4. washThe mixture was washed with chloroform, to which
  5. additionwas added
  6. stirringwhile stirring at room temperature
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water and ether

Sources & evidence

ORD record
ord-7c2abcb172a5419d948bba33d9fc3c16
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

Loading…