Sulfuric Acid → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester

HRID 964577Notes

Reaction equation

HRID 964577 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.[CH3:24][CH2:25][O:26][C:27]([CH2:29][C:30]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=O)=[O:28].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:25]([O:26][C:27](=[O:28])[CH2:29][C:30]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)[C:3]2[C:2](=[CH:19][C:18]([O:20][CH3:21])=[C:17]([O:22][CH3:23])[CH:16]=2)[N:1]=1)[CH3:24]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 66045Diethyl acetonedicarboxylateHCID 99269672-Amino-4,5,3',4'-tetramethoxybenzophenone

Product 1

HCID 117990276,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl esterYield 73%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-4,5,3',4'-tetramethoxybenzophenone (50.0 g), acetonedicarboxylic acid diethyl ester (35.0 g) and acetic acid (400 ml), concentrated sulfuric acid (1.5 ml) was added, followed by stirring at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured over water, neutralized with a saturated aqueous sodium hydrogen carbonate solution and then extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), after which the solvent was distilled off under reduced pressure. The residual crystal was recrystallized from ethanol to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-3-ethoxycarbonylquinoline-2-acetic acid ethyl ester (55.6 g, 73%) as a colorless prismatic crystal having a melting point of 146° to 147° C.

Workup

  1. additionwas added
  2. concentrationThe 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 under reduced pressure
  8. customThe residual crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-bdc26299d6ce4696833890c3ce3c6c92
Source dataset
uspto-grants-1998_06
Patent number
US05770602

Reaction notes

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