Glycerol → 5-Methyl-8-nitroquinoline

HRID 513385Notes

Reaction equation

HRID 513385 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].O[CH2:13][CH:14]([CH2:16]O)O.[Na+].[N+](C1C=C(S([O-])(=O)=O)C=CC=1)([O-])=O.OS(O)(=O)=O.O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]2[C:8]=1[CH:13]=[CH:14][CH:16]=[N:7]2

Participants

5

Reactant 4

HCID 753GlycerolHCID 113566-Nitro-m-toluidineHCID 31389Sodium 3-nitrobenzenesulfonateHCID 21910475Sulfuric acid hydrate (1:1)

Product 1

HCID 64278395-Methyl-8-nitroquinolineYield 77%

Conditions

Temperature
105 °C

Procedure

5-methyl-2-nitroaniline (1.0 g, 6.57 mmol), glycerol (1.88 g, 20.4 mmol), 3-nitrobenzenesulfonic acid sodium salt (1.92 g, 8.54 mmol) were added to H2SO4/H2O (6 ml, 7:5) solution and heated at 105° C. for 48 h. After completion of the reaction (monitored by LCMS), the mixture was cooled to 45° C. and poured slowly onto ice water (50 ml) and the mixture was extracted with DCM. The combined organic phases were dried (Na2SO4) and concentrated in vacuo to give the title compound (950 mg, 77%) which was used in the next step without purification.

Workup

  1. customAfter completion of the reaction (monitored by LCMS)
  2. temperaturethe mixture was cooled to 45° C.
  3. additionpoured slowly onto ice water (50 ml)
  4. extractionthe mixture was extracted with DCM
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cd3903bd707449d9bc84035a949d405
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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