Glycerol → 7-Methoxy-6-nitro-quinoline

HRID 1773558Notes

Reaction equation

HRID 1773558 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].O=[As](O[As](=O)=O)=O.O[CH2:21][CH:22]([CH2:24]O)O.S(=O)(=O)(O)O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([CH:21]=[CH:22][CH:24]=[N:12]2)=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 14771Arsenic pentoxideHCID 27557953-Methoxy-4-nitroaniline

Product 1

HCID 580563217-Methoxy-6-nitro-quinolineYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-methoxy-4-nitro-phenylamine (13.4 g, 80.0 mmol), arsenic pentoxide (11.0 g, 48.0 mmol) and glycerol (33 mL, 216.0 mmol) at 100° C., was added, dropwise, concentrated sulfuric acid (4.7 mL, 88.0 mmol). The reaction mixture was then heated at a temperature ranging between 150 and 160° C. for 2 hours and then was cooled. Water (200 mL) was added and the resulting mixture was extracted four times with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc) to give 9.00 g (61% yield) of 7-methoxy-6-nitro-quinoline as an orange solid.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was then heated at a temperature
  3. temperaturewas cooled
  4. extractionthe resulting mixture was extracted four times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude residue was purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-53a37f62029648118585d3d849a80112
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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