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

HRID 341826Notes

Reaction equation

HRID 341826 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][C:7]2=[O:12].[C:13]1([CH2:19][CH2:20][CH:21]=O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CO>[C:13]1([CH2:19][CH2:20][C:21]2[N:10]3[C:11]4[C:6]([C:7](=[O:12])[CH2:8][CH2:9]3)=[CH:5][CH:4]=[CH:3][C:2]=4[N:1]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7707BenzenepropanalHCID 122973664(1H)-Quinolinone, 8-amino-2,3-dihydro-

Product 1

HCID 158384624,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]-quinolin-6-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fifteen grams of 8-amino-2,3-dihydro-4(1H) -quinolinone was dissolved in methanol (300 mL), and after addition of 3-phenylpropionaldehyde (14.6 mL) and 1N HCl (3 mL), the mixture was stirred at room temperature for 2 hrs, followed by addition of silica gel (60 g) to the reaction mixture, and the solvent was removed under reduced pressure. The residue was heated at 100° C. for 2 hrs and purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to yield the titled compound as yellow crystals (13.2 g).

Workup

  1. additionfollowed by addition of silica gel (60 g) to the reaction mixture
  2. customthe solvent was removed under reduced pressure
  3. temperatureThe residue was heated at 100° C. for 2 hrs
  4. custompurified by silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a9c4227919b54ea4832e4ff9ece6810a
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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