Hydrochloric Acid → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

HRID 341833Notes

Reaction equation

HRID 341833 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[C:12]1([CH2:18][CH2:19][CH:20]=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>CO>[C:12]1([CH2:18][CH2:19][C:20]2[N:10]3[C:11]4[C:6]([CH2:7][CH2:8][CH2:9]3)=[CH:5][CH:4]=[CH:3][C:2]=4[N:1]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 1046728-Quinolinamine, 1,2,3,4-tetrahydro-

Product 1

HCID 158384635,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Thirty-five grams of 8-amino-1,2,3,4-tetrahydroquinoline was dissolved in methanol (700 mL) and, following the addition of 3-phenylpropionaldehyde (37.4 mL) and 1N HCl (7 mL) and subsequent stirring at room temperature for 1 hr, silica gel (75 g) was added to the reaction solution and the solvent was removed under reduced pressure. The residue was heated at 100° C. for 1 hr, purified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate) and recrystallized with ethyl acetate to yield the titled compound as pale yellow crystals (19.3 g).

Workup

  1. additionsilica gel (75 g) was added to the reaction solution
  2. customthe solvent was removed under reduced pressure
  3. temperatureThe residue was heated at 100° C. for 1 hr
  4. custompurified by silica gel column chromatography (eluent: dichloromethane/ethyl acetate)
  5. customrecrystallized with ethyl acetate

Sources & evidence

ORD record
ord-73f3c5abdc1a498c9e54f3864ff76f44
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

Loading…