Quinoline → HCID 178516363, compound

HRID 1579910Notes

Reaction equation

HRID 1579910 reaction equation
[OH: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]=1C(O)=O.N1C2C(=CC=CC=2)C=CC=1>CCOCC>[CH2:13]1[O:14][C:8]2[CH:7]=[C:6]3[C:11]([C:2]([OH:1])=[CH:3][CH:4]=[N:5]3)=[CH:10][C:9]=2[O:12]1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 178524696HCID 178524696, compound

Product 1

HCID 178516363HCID 178516363, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 50 g. of 4-hydroxy-6,7-methylenedioxyquinoline-3-carboxylic acid in 500 ml. of freshly distilled quinoline was heated at 200° until the evolution of gas ceased. The reaction mixture was cooled to room temperature, diluted with an equal amount of ether and kept cool overnight. The precipitated brown solid (51.4 g., m.p. 254°-267°) was collected by filtration and dissolved in refluxing ethanol. The insoluble material was removed and the ethanol solution was reduced to one-third of its volume. The solution was diluted with an equal amount of ether. On cooling, 31.1 g. of 6,7-methylenedioxy-4-quinolinol separated, m.p. 280°-282°. Recrystallization (2x) from hot water yielded analytically pure 6,7-methylenedioxy-4-quinolinol as a pale yellow solid, m.p. 288°-289° .

Workup

  1. additionA suspension of 50 g
  2. temperaturekept cool overnight
  3. filtrationThe precipitated brown solid (51.4 g., m.p. 254°-267°) was collected by filtration
  4. dissolutiondissolved
  5. temperaturein refluxing ethanol
  6. customThe insoluble material was removed
  7. additionThe solution was diluted with an equal amount of ether
  8. temperatureOn cooling
  9. customof 6,7-methylenedioxy-4-quinolinol separated
  10. customRecrystallization (2x) from hot water

Sources & evidence

ORD record
ord-af22cbab2e074d22a1171d1da2d23229
Source dataset
uspto-grants-1976_01
Patent number
US03931192

Reaction notes

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