Ethyl 8-ethoxy-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate → HCID 15618563, compound

HRID 1658349Notes

Reaction equation

HRID 1658349 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:17]([O:19]CC)=[O:18])[CH3:2]>[OH-].[Na+]>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][C:10]3[O:16][CH2:15][O:14][C:11]=3[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:17]([OH:19])=[O:18])[CH3:2]

Participants

3

Reactant 1

HCID 12367717Ethyl 8-ethoxy-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

Product 1

HCID 15618563HCID 15618563, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To 120 ml of 5% ethanolic sodium hydroxide solution was added 6 g of ethyl 4-ethoxy-6,7-methylenedioxyquinoline-3-carboxylate with stirring, and the mixture was stirred further for 15 minutes at room temperature then concentrated to a small volume under reduced pressure. A small amount of water was added to the residue, the pH of the solution was adjusted to 5 by the addition of hydrochloric acid, and the precipitate thus formed was filtered, washed with water and dried to provide 5.2 g of almost pure 4-ethoxy-6,7-methylenedioxyquinoline-3-caboxylic acid having a melting point of 250°-253°C. Recrystallization from dimethyl sulfoxide gave colorless needles having a melting point of 252°C (decomposed).

Workup

  1. stirringthe mixture was stirred further for 15 minutes at room temperature
  2. concentrationthen concentrated to a small volume under reduced pressure
  3. additionA small amount of water was added to the residue
  4. additionthe pH of the solution was adjusted to 5 by the addition of hydrochloric acid
  5. customthe precipitate thus formed
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-cfe8cd3e5cdc4922b24905033b63633b
Source dataset
uspto-grants-1976_06
Patent number
US03963736

Reaction notes

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