Glycerol → 6-Quinolinecarboxylic acid

HRID 449243Notes

Reaction equation

HRID 449243 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[N+]([C:14]1[CH:19]=CC(O)=C[CH:15]=1)([O-])=O.S(=O)(=O)(O)O.OCC(CO)O.[OH-].[Na+]>>[N:1]1[C:2]2[C:10](=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH:19]=[CH:14][CH:15]=1

Participants

6

Reactant 5

HCID 753GlycerolHCID 9784-Aminobenzoic AcidHCID 9804-NitrophenolHCID 1118Sulfuric AcidHCID 14798Sodium Hydroxide

Product 1

HCID 825716-Quinolinecarboxylic acidYield 112.8%

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-aminobenzoic acid (175 g, 1.28 mol), 4-nitrophenol (88.75 g, 0.64 mol) and sulphuric acid (1.2 lit.), glycerol (234.8 g, 2.55 mol) was added dropwise at 135° C. After 48 h, the reaction mixture was cooled to 0° C. and the pH adjusted to 3-5 with 10% sodium hydroxide solution. The resulting precipitate was collected by filtration and washed with water and dried under vacuum to afford the title compound as a black solid (125 g, 56%).

Workup

  1. additionwas added dropwise at 135° C
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-84cbdd497d024a73854bcd37608df9d5
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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