Sulfuric Acid → HCID 22097606, compound

HRID 1584157Notes

Reaction equation

HRID 1584157 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[CH:16][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=O.[CH2:24]([O:26][C:27](=[O:39])[CH2:28][C:29](=O)[CH2:30][CH2:31][CH2:32][N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)[CH3:25].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:24]([O:26][C:27]([C:28]1[C:29]([CH2:30][CH2:31][CH2:32][N:33]2[CH:37]=[CH:36][N:35]=[CH:34]2)=[N:1][C:2]2[C:3]([C:4]=1[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=1)=[CH:16][C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)=[O:39])[CH3:25]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenoneHCID 22097627Ethyl β-oxo-1H-imidazole-1-hexanoate

Product 1

HCID 22097606HCID 22097606, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (453 mg), 6-(1-imidazolyl)-3-oxohexanoic acid ethyl ester (320 mg) and acetic acid (5 ml), concentrated sulfuric acid (0.03 ml) was added, followed by stirring at 100° C. for 2 hours. After the reaction mixture was concentrated under reduced pressure, the residue was poured over water, alkalinized with 2 N sodium hydroxide and then extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), after which the solvent was distilled off. The residual oily substance was subjected to silica gel column chromatography and eluted with chloroform-methanol (50:1, v/v) to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-[3-(1-imidazolyl)propyl]quinoline-3-carboxylic acid ethyl ester (310.0 mg, 43%), which was then recrystallized from ethyl acetate-hexane to yield a colorless prismatic crystal having a melting point of 164 to 165° C.

Workup

  1. additionwas added
  2. concentrationAfter the reaction mixture was concentrated under reduced pressure
  3. additionthe residue was poured over water
  4. extractionextracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialdried (MgSO4)
  7. distillationafter which the solvent was distilled off
  8. washeluted with chloroform-methanol (50:1

Sources & evidence

ORD record
ord-00a40bbf90094960b9e79f40a1b0fd23
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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