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

HRID 619536Notes

Reaction equation

HRID 619536 reaction equation
[C:1]([C:6]1[N:10]2[C:11]([NH2:15])=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][CH:7]=1)(OCC)=[O:2].C[O-].[Na+].CO.Cl>C(#N)C>[NH:15]1[C:11]2[N:10]3[C:9](=[N:8][CH:7]=[C:6]3[C:1]1=[O:2])[CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21823562Ethyl 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 180%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution prepared by dissolving 1.44 g (7.0 mM) of 3-carbethoxy-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-631e4e2930f447f1994b4f5b9c11049e
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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