Oxolinic acid → 3-Quinolinecarboxylic acid, 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxo-

HRID 2253592Notes

Reaction equation

HRID 2253592 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]3[O:15]C[O:13][C:10]=3[CH:11]=2)[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].B(Br)(Br)Br.[OH-].[K+]>O>[OH:15][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][C:10]=1[OH:13])[N:3]([CH2:1][CH3:2])[CH:4]=[C:5]([C:17]([OH:19])=[O:18])[C:6]2=[O:16]

Participants

5

Reactant 3

HCID 4628Oxolinic acidHCID 14797Potassium HydroxideHCID 25134Boron tribromide

Product 1

HCID 54930183-Quinolinecarboxylic acid, 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxo-Yield 84.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.4-Dihydro-1-ethyl-6,7-methylenedioxy-4-oxoquinoline-3-carboxylic acid (3.9 g) and boron tribromide (15 ml) were heated at 50° C. for 15 hours. The reaction mixture was cooled and added slowly to water (100 ml) at 0° C. The pH was adjusted to 11 with concentrated potassium hydroxide, the mixture was filtered and the filtrate taken to pH1, whereupon the precipitate was collected by filtration, washed with water and dried to give 1,4-dihydro-6,7-dihydroxy-1-ethyl-4-oxoquinoline-3-carboxylic acid (3.13 g); δ ((CD3)2SO) 1.42(3H,t); 4.46(2H,q); 7.23(1H,s); 7.66(1H,s); 8.82(1H,s)ppm.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationthe mixture was filtered
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0872327a78f3481b8092275f8f211e95
Source dataset
uspto-grants-1993_08
Patent number
US05232918

Reaction notes

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