Acetic Acid → 8-Methyl-7-nitroquinoline
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.[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]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2-methyl-3-nitroaniline (10 g), glycerin (20.57 g) and As2O5.xH2O (Baker, 88% As2O5, 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.
Workup
- temperatureThe resulting mixture is cooled to room temperature
- waitAfter about 10 minutes
- extractionextracted with CH2Cl2 (3×200 mL)
- washThe combined extracts are washed with H2O (200 mL), sat. NaHCO3 (200 mL)
- dry with materialdried over MgSO4 and rotary evaporated
- filtrationThe crude quinoline is filtered through a short pad of silica gel
- customThe filtrate is rotary evaporated
- customthe residue recrystallized from hexane/CH2Cl2
Sources & evidence
- ORD record
- ord-f7c634dda55a41e5a5589b8bec74e3b2
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576437
Reaction notes
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