Sulfuric Acid → HCID 10765689, compound

HRID 617209Notes

Reaction equation

HRID 617209 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[CH:24]=[C:23]2[O:25][CH2:26][CH2:27][O:28][C:22]2=[CH:21][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)=O.[Cl:29][CH2:30][C:31](=O)[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>C(O)(=O)C>[Cl:29][CH2:30][C:31]1[C:32]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[C:8]2[C:7](=[CH:24][C:23]3[O:25][CH2:26][CH2:27][O:28][C:22]=3[CH:21]=2)[N:6]=1

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

Conc. sulfuric acid (0.3 ml) was added to a mixture of 2-amino-3',4'-dimethoxy-4,5-ethylenedioxybenzophenone (6.5 g), ethyl 4-chloroacetoacetate (3.7 g) and acetic acid (60 ml), and the resulting mixture was stirred at 100° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured into water. The mixture was made alkaline with 2N NaOH and extracted with chloroform. The chloroform layer was washed with water and dried (MgSO4), and the solvent was distilled off under reduced pressure. The residue was subjected to column chromatography on silica gel. From the fraction eluted with chloroform/ethyl acetate (7:3, v/v), ethyl 2-chloromethyl-4- (3,4-dimethoxyphenyl)-6,7-ethylenedioxyquinoline-3-carboxylate (5.5 g, 60%) was obtained and recrystallized from acetone.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was poured into water
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried (MgSO4)
  6. distillationthe solvent was distilled off under reduced pressure
  7. washFrom the fraction eluted with chloroform/ethyl acetate (7:3

Sources & evidence

ORD record
ord-f61bd5ff1adb4a78930e76ed30dd7528
Source dataset
uspto-grants-1999_09
Patent number
US05948782

Reaction notes

Loading…