1,4-Dioxane → HCID 178479751, compound

HRID 1826909Notes

Reaction equation

HRID 1826909 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([O:17]CC)=[O:16].[O:20]1CCOCC1>>[ClH:1].[OH:20][C:2]1[C:11]2[C:6](=[CH:7][C:8]3[O:14][CH2:13][O:12][C:9]=3[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:15]([OH:17])=[O:16]

Participants

3

Reactant 2

HCID 312751,4-DioxaneHCID 824579ethyl 8-chloro[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

Product 1

HCID 178479751HCID 178479751, compound

Procedure

Ethyl 4-chloro-6,7-methylenedioxyquinoline-3-carboxylate (18.5 g, 66.2 mmol) was dissolved in dioxane (100 mL) and treated with 50 mL 5 NNaOH and heated at reflux for 2 hour. After this time the solution was concentrated on a rotary evaporator, cooled and extracted with dichloromethane (2×100 mL). The remaining aqueous solution was then acidified with concentrated HCl and the precipitate collected and dried to afford 7 g of crude 4-hydroxy-6,7-methylenedioxyquinoline-3-carboxylic acid hydrochloride.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hour
  3. concentrationAfter this time the solution was concentrated on a rotary evaporator
  4. temperaturecooled
  5. extractionextracted with dichloromethane (2×100 mL)
  6. customthe precipitate collected
  7. customdried

Sources & evidence

ORD record
ord-8f7fa91b84384c239207573cd35e246f
Source dataset
uspto-grants-2006_05
Patent number
US07053104B2

Reaction notes

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