Ethylenediamine → Imidazo(1,2-a)pyridin-5(1H)-one, 2,3-dihydro-7-phenyl-

HRID 1785463

Reaction equation

HRID 1785463 reaction equation
C(O[C:4](=[O:16])[CH2:5][C:6]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:7][C:8]#[N:9])C.[CH2:17](N)[CH2:18][NH2:19]>>[C:10]1([C:6]2[CH:7]=[C:8]3[NH:9][CH2:17][CH2:18][N:19]3[C:4](=[O:16])[CH:5]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 540877674-Cyano-3-phenyl-but-3-enoic acid ethyl ester

Product 1

HCID 3050276Imidazo(1,2-a)pyridin-5(1H)-one, 2,3-dihydro-7-phenyl-

Conditions

Temperature
160 °C

Procedure

4-Cyano-3-phenyl-but-3-enoic acid ethyl ester (crude, 9.37 g, 0.043 mol), ethylenediamine (3 mL, 0.043 mol) were mixed in dichlorobenze (20 mL) and heated at 160° C. overnight. The resulting suspension was cooled to room temperature, filtered, and the filtrated cake was washed with EtOAc and finally dried to provide the title compound as a brownish yellow solid. MS m/e 213 (M+H)+.

Workup

  1. temperatureThe resulting suspension was cooled to room temperature
  2. filtrationfiltered
  3. washthe filtrated cake was washed with EtOAc
  4. customfinally dried

Sources & evidence

ORD record
ord-ee5713a5f957405987c2c19d732f5004
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Linked notes

Loading…