Glycerol → 6-Quinolinecarboxylic acid

HRID 881042Notes

Reaction equation

HRID 881042 reaction equation
S(=O)(=O)(O)[OH:2].[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]C(O)=O)=[CH:9][CH:8]=1.O[CH2:18][CH:19]([CH2:21][OH:22])O.II>>[N:6]1[C:7]2[C:12](=[CH:18][C:19]([C:21]([OH:22])=[O:2])=[CH:9][CH:8]=2)[CH:11]=[CH:10][CH:13]=1

Participants

5

Reactant 4

HCID 753GlycerolHCID 807IodineHCID 1118Sulfuric AcidHCID 145334-Aminophenylacetic acid

Product 1

HCID 825716-Quinolinecarboxylic acid

Conditions

Temperature
140 °C

Procedure

Sulphuric acid (67.5 ml) was added to 4-Aminophenylacetic acid (45 g, 297 mmol), glycerol (61.7 g, 67 mmol), and iodine (1.14 g, 4 mmol) drop-wise at rt. The mixture was heated to 140° C. for 5 h. After that reaction mixture quenched with ice and solid that formed was filtered Solid was dissolved in MeOH and charcoal was added to it and refluxed for 1 h. This mixture was filtered through celite and methanol was removed to obtain the title compound (7 g) as a brown solid.

Workup

  1. customAfter that reaction mixture quenched with ice and solid
  2. customthat formed
  3. filtrationwas filtered Solid
  4. dissolutionwas dissolved in MeOH
  5. additioncharcoal was added to it
  6. temperaturerefluxed for 1 h
  7. filtrationThis mixture was filtered through celite and methanol
  8. customwas removed

Sources & evidence

ORD record
ord-76983d573e074743956a7e3c8511b65e
Source dataset
uspto-grants-2015_03
Patent number
US08993612B2

Reaction notes

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