p-Toluenesulfonic acid → HCID 3504015, compound

HRID 1658347Notes

Reaction equation

HRID 1658347 reaction equation
C([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][CH2:20][CH3:21])=[O:18])C.[C:22]1(C)C=CC(S(O)(=O)=O)=C[CH:23]=1>C(Cl)(Cl)Cl>[CH2:22]([N:7]1[C:8]2[C:13](=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[C:4](=[O:3])[C:5]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6]1)[CH3:23]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 12367717Ethyl 8-ethoxy-2H-[1,3]dioxolo[4,5-g]quinoline-7-carboxylate

Product 1

HCID 3504015HCID 3504015, compoundYield 5,655.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 2.9 g of ethyl 4-ethoxy-6,7-methylenedioxyquinoline 3-carboxylate and 0.03 g of p-toluenesulfonic acid was melted and heated at 180°C (bath temperature) for 2 hours and cooled. The product was dissolved in chloroform, washed with a dilute aqueous sodium carbonate solution and then with water. The chloroform layer was separated and evaporated to dryness. There was obtained 2.85 g of pure ethyl 1-ethyl-6,7-methylenedioxy-4-quinolone-3-carboxylate, m.p. 175°-177°C.

Workup

  1. temperaturecooled
  2. washwashed with a dilute aqueous sodium carbonate solution
  3. customThe chloroform layer was separated
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-6a7ae9df64314cb5add22245f5e2b62a
Source dataset
uspto-grants-1976_06
Patent number
US03963736

Reaction notes

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