Glycerol → 8-Methyl-7-nitroquinoline

HRID 1416896Notes

Reaction equation

HRID 1416896 reaction equation
[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].O[CH2:13][CH:14]([CH2:16]O)O.O.O=[As](O[As](=O)=O)=O.[OH-].[NH4+]>S(=O)(=O)(O)O.O.C(O)(=O)C>[CH3:1][C:2]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[C:5]2[C:3]=1[N:4]=[CH:16][CH:14]=[CH:13]2

Participants

8

Reactant 4

HCID 753GlycerolHCID 117832-Methyl-3-nitroanilineHCID 14923Ammonium HydroxideHCID 16211720Arsenic(V) oxide hydrate

Product 1

HCID 2541658-Methyl-7-nitroquinoline

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-methyl-3-nitroaniline (10 g), glycerin (20.57 g) and arsenic pentoxide hydrate (As2O5.xH2O, Baker, 88% As2O5, 8.5 g) in concentrated sulfuric acid (9.75 mL) is heated slowly to 150° C. in an open round-bottom flask, then stirred for 6 hours at 150° C. The resulting mixture is cooled to room temperature and diluted with water (200 mL), then basified with ammonium hydroxide (28-30%, 100 mL). After about 10 minutes, the solution is acidified to pH=5 with glacial acetic acid and extracted with methylene chloride (3×200 mL). The combined extracts are washed with water (200 mL) and saturated sodium bicarbonate (200 mL), then dried over magnesium sulfate and rotary evaporated. The crude quinoline is filtered through a short pad of silica gel, using methylene chloride as solvent. The filtrate is rotary evaporated and the residue recrystallized from hexanes/methylene chloride to afford 8-methyl-7-nitroquinoline as a tan solid.

Workup

  1. temperatureThe resulting mixture is cooled to room temperature
  2. waitAfter about 10 minutes
  3. extractionextracted with methylene chloride (3×200 mL)
  4. washThe combined extracts are washed with water (200 mL) and saturated sodium bicarbonate (200 mL)
  5. dry with materialdried over magnesium sulfate and rotary evaporated
  6. filtrationThe crude quinoline is filtered through a short pad of silica gel
  7. customThe filtrate is rotary evaporated
  8. customthe residue recrystallized from hexanes/methylene chloride

Sources & evidence

ORD record
ord-8b1d54c1327343b0aecee1f3a2bf3c98
Source dataset
uspto-grants-1999_06
Patent number
US05916900

Reaction notes

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