Sulfuric Acid → HCID 10765689, compound

HRID 266114Notes

Reaction equation

HRID 266114 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-4,5-ethylenedioxy-3',4'-dimethoxybenzophenone (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. The residue was poured into water and made alkaline with 2N sodium hydroxide, and extracted with chloroform. The chloroform layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. 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-6,7-ethylenedioxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (5.5 g, 60%). This compound was recrystallized from acetone. Colorless prisms, mp. 197°-198° C.

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 over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethyl acetate (7:3

Sources & evidence

ORD record
ord-c44f1695b3f14ff39981b1243d3c2104
Source dataset
uspto-grants-1997_07
Patent number
US05650410

Reaction notes

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