ethyl 8-chloro[1,3]dioxolo[4,5-g]quinoline-7-carboxylate → Ethyl 8-ethoxy-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

HRID 1658344Notes

Reaction equation

HRID 1658344 reaction equation
Cl[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][CH2:18][CH3:19])=[O:16].[CH3:20][CH2:21][O-:22].[Na+]>C(O)C>[CH2:21]([O:22][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][CH2:18][CH3:19])=[O:16])[CH3:20]

Participants

4

Reactant 2

HCID 824579ethyl 8-chloro[1,3]dioxolo[4,5-g]quinoline-7-carboxylateHCID 2723922Sodium ethoxide2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture containing 126 g of ethyl 4-chloro-6,7-methylenedioxyquinoline-3-carboxylate and 200 ml of absolute ethanol was added dropwise an ethanolic sodium ethylate solution prepared from 34 g of sodium ethylate and 250 ml of ethanol with stirring. The resulting mixture was refluxed for 1.5 hours and the ethanol was removed under reduced pressure. The residue was poured into ice-water, the insoluble solid was filtered, washed with water and dried to provide 126 g of almost pure ethyl 4-ethoxy-6,7-methylenedioxyquinoline-3-caboxylate, m.p. 84°-86°C. Recrystallization from petroleum ether gave colorless needles, m.p. 85°-85.5°C.

Workup

  1. temperatureThe resulting mixture was refluxed for 1.5 hours
  2. customthe ethanol was removed under reduced pressure
  3. additionThe residue was poured into ice-water
  4. filtrationthe insoluble solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-e3a8369334a64b4799716e09c59b6819
Source dataset
uspto-grants-1976_06
Patent number
US03963736

Reaction notes

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