Hydrochloric Acid → 1,2-Dihydro-1,4,7b-triazacyclopent[cd]inden-2-one

HRID 1068823Notes

Reaction equation

HRID 1068823 reaction equation
[C:1]([C:5]1[N:9]2[C:10]([NH2:14])=[CH:11][CH:12]=[CH:13][C:8]2=[N:7][CH:6]=1)(OC)=[O:2].C[O-].[Na+].CO.Cl>C(#N)C>[NH:14]1[C:10]2[N:9]3[C:8](=[N:7][CH:6]=[C:5]3[C:1]1=[O:2])[CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21190256Methyl 5-aminoimidazo[1,2-a]pyridine-3-carboxylateHCID 23694274Sodium methanolate methanol

Product 1

HCID 117449051,2-Dihydro-1,4,7b-triazacyclopent[cd]inden-2-oneYield 167.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution prepared by dissolving 1.44 g (7.0 mM) of 3-carbomethoxy-5-aminoimidazo[1,2-a]pyridine in 10 ml of acetonitrile followed by addition of 3.2 ml (14.0 mM) of 25% sodium methoxide-methanol and the mixture was refluxed for 1 hour. After completion of the reaction, 1.15 ml (14.0 mM) of 12N-hydrochloric acid was added to the reaction mixture under ice-cooling and the solvent was thoroughly distilled off under reduced pressure to provide 2.01 g (yield 100%) of a crude product as tan-colored solid.

Workup

  1. customTo a solution prepared
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionwas added to the reaction mixture under ice-
  4. temperaturecooling
  5. distillationthe solvent was thoroughly distilled off under reduced pressure

Sources & evidence

ORD record
ord-5bc9ebc966a049fbbb39d7ab1874fb36
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

Loading…