Sulfuric Acid → HCID 10765689, compound

HRID 1584137Notes

Reaction equation

HRID 1584137 reaction equation
[NH2:1][C:2]1[CH:19]=[C:18]2[O:20][CH2:21][CH2:22][O:23][C:17]2=[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.[Cl:24][CH2:25][C:26](=O)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].S(=O)(=O)(O)O>C(O)(=O)C>[CH2:31]([O:30][C:28]([C:27]1[C:26]([CH2:25][Cl:24])=[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]1[O:23][CH2:22][CH2:21][O:20][C:18]=1[CH:19]=2)=[O:29])[CH3:32]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 21851148HCID 21851148, compound

Product 1

HCID 10765689HCID 10765689, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 2-amino-3',4'-dimethoxy-4,5-ethylenedioxybenzo-phenone (6.5 g), ethyl 4-chloroacetoacetate (3.7 g) and acetic acid (60 ml), concentrated sulfuric acid (0.3 ml) was added, followed by stirring at 100° C. for 3 hours. After the reaction mixture was concentrated under reduced pressure, the residue was poured over water and alkalinized with 2 N NaOH 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 residue was subjected to silica gel column chromatography and eluted with chloroform-ethyl acetate (7:3, v/v) to yield 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-ethylenedioxyquinoline-3-carboxylic acid ethyl ester (5.5 g, 60%), which was then recrystallized from acetone to yield a colorless prismatic crystal having a melting point of 197 to 198° 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 under reduced pressure
  8. washeluted with chloroform-ethyl acetate (7:3

Sources & evidence

ORD record
ord-c06e57bf10714e3f8fc468de67e7d72d
Source dataset
uspto-grants-1999_08
Patent number
US05932592

Reaction notes

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