2-Methyl-8-nitroquinoline → 2-Methyl-8-nitroquinolin-7-amine

HRID 868958

Reaction equation

HRID 868958 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[I-].C[N+:17](C)(C)N.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CS(C)=O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([N+:12]([O-:14])=[O:13])[C:6]([NH2:17])=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 4

HCID 134332-Methyl-8-nitroquinolineHCID 18683Hydrazinium, 1,1,1-trimethyl-, iodide (1:1)HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 700972812-Methyl-8-nitroquinolin-7-amineYield 14.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 2-methyl-8-nitroquinoline (1.88 g, 10 mmol) and 1,1,1-trimethylhydrazinium iodide (3.03 g, 15 mmol) in anhydrous dimethyl sulfoxide (20 mL) was added potassium tert-butoxide as a solid (3.36 g, 30 mmol). The mixture was stirred at room temperature for 1 h. The mixture was then poured into saturated aqueous ammonium chloride, and extracted with EtOAc. The organic layer was concentrated and purified by column chromatography to give 2-methyl-8-nitroquinolin-7-amine as a yellow solid (300 mg).

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-05e1fa67160244eb83cd940eecb11d1f
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Linked notes

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