2-Chlorobenzaldehyde → 4-(2-Chlorophenyl)-3-ethoxycarbonyl-2-[2-(2-n-propylimidazol-1-yl)propoxymethyl]-1,4,5,6,7,8-hexahydro-5-oxoquinoline

HRID 1721879Notes

Reaction equation

HRID 1721879 reaction equation
[CH2:1]([C:4]1[N:5]([CH:9]([CH3:21])[CH2:10][O:11][CH2:12][C:13](=O)[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:6]=[CH:7][N:8]=1)[CH2:2][CH3:3].[NH2:22][C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1.[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]=O>C(O)C>[Cl:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH:33]1[C:24]2[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C:23]=2[NH:22][C:13]([CH2:12][O:11][CH2:10][CH:9]([N:5]2[CH:6]=[CH:7][N:8]=[C:4]2[CH2:1][CH2:2][CH3:3])[CH3:21])=[C:14]1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 788923-Aminocyclohex-2-en-1-oneHCID 20070369Ethyl 4-[2-(2-propylimidazol-1-yl)propoxy]-3-ketobutanoate

Product 1

HCID 200703824-(2-Chlorophenyl)-3-ethoxycarbonyl-2-[2-(2-n-propylimidazol-1-yl)propoxymethyl]-1,4,5,6,7,8-hexahydro-5-oxoquinolineYield 22%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-[2-(2-n-propylimidazol-1-yl)propoxy]-3-ketobutanoate (590 mg), 3-aminocyclohex-2-enone (220 mg) and 2-chlorobenzaldehyde (281 mg) were stirred in refluxing ethanol (8 ml) for 8 hours. The solvent was removed under reduced pressure. The crude product was chromatographed over silica eluting with a mixture of diethylamine and ethyl acetate (1:49). The solvents were removed in vacuo and the residue rechromatographed over silica eluting with a mixture of methanol and ethyl acetate [1:9]. The solvents were removed in vacuo. The resulting foam was stirred in ether overnight, the solid filtered and dried in vacuo yielding the title compound as a white solid 220 mg (22%). M.p. 127°-131° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was chromatographed over silica eluting with a mixture of diethylamine and ethyl acetate (1:49)
  3. customThe solvents were removed in vacuo
  4. customthe residue rechromatographed over silica eluting with a mixture of methanol and ethyl acetate [1:9]
  5. customThe solvents were removed in vacuo
  6. filtrationthe solid filtered
  7. customdried in vacuo

Sources & evidence

ORD record
ord-bb07fe0403f4497fa50f0eabbbffa9e2
Source dataset
uspto-grants-1989_08
Patent number
US04853392

Reaction notes

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