Acetic Acid → 8-Methyl-7-nitroquinoline

HRID 861926Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 861926
[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.[OH-].[NH4+].C(O)(=O)C>O>[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

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 753GlycerolHCID 117832-Methyl-3-nitroanilineHCID 14923Ammonium Hydroxide

Produkt 1

HCID 2541658-Methyl-7-nitroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-methyl-3-nitroaniline (10 g), glycerin (20.57 g) and As2O5.xH2O (Baker, 88% As2 O5, 8.5 g) is heated slowly to 150° C. in an open round-bottom flask, then stirred for 6 hrs 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 CH2Cl2 (3×200 mL). The combined extracts are washed with H2O (200 mL), sat. NaHCO3 (200 mL), then dried over MgSO4 and rotary evaporated. The crude quinoline is filtered through a short pad of silica gel, using CH2Cl2 as solvent. The filtrate is rotary evaporated and the residue recrystallized from hexane/CH2Cl2 to afford 8-methyl-7-nitroquinoline as a tan solid.

Aufarbeitung

  1. temperatureThe resulting mixture is cooled to room temperature
  2. waitAfter about 10 minutes
  3. extractionextracted with CH2Cl2 (3×200 mL)
  4. washThe combined extracts are washed with H2O (200 mL), sat. NaHCO3 (200 mL)
  5. dry with materialdried over MgSO4 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 hexane/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-be0c7712ed52410faa74a7744ec92970
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716966

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