Sulfuric Acid → HCID 10765689, compound

HRID 1458902Notes

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

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 mixture was stirred at 100° C. for 3 hours. The reaction mixture was concentrated under reduced pressure, and the residue was poured into water, made alkaline with 2N sodium hydroxide and extracted with chloroform. The chloroform layer was washed with water and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform/ethyl acetate (=7/3, v/v) gave ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-ethylenedioxyquinoline-3-carboxylate (5.5 g, 60%) which was then recrystallized from acetone.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
additionthe residue was poured into water
extractionextracted with chloroform
washThe chloroform layer was washed with water
dry with materialdried over MgSO4
customThe solvent was evaporated under reduced pressure
washThe fractions eluted with chloroform/ethyl acetate (=7/3

Sources & evidence

ORD record: ord-664c16f2175d474ab8de09a76e7ec51b
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05852039

Reaction notes

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