Water → N-Methyl-8-nitroquinolin-7-amine

HRID 1772000Notes

Reaction equation

HRID 1772000 reaction equation
[N+:1]([C:4]1[C:5]([NH2:14])=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[H-].[Na+].I[CH3:18].O>O1CCCC1>[CH3:18][NH:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[C:13]2[C:8]([CH:9]=[CH:10][CH:11]=[N:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 129549938-Nitroquinolin-7-amine

Product 1

HCID 29985233N-Methyl-8-nitroquinolin-7-amineYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-nitroquinolin-7-amine (1.89 g, 10 mmol) in tetrahydrofuran (THF) (10 mL) was added sodium hydride (60% wt in mineral oil, 800 mg, 20 mmol). The mixture was stirred at room temperature for 30 minutes, then iodomethane (1.42 g, 10 mmol) was added. The mixture was stirred at room temperature for 5 h. Then water (10 mL) was added. The mixture was extracted with EtOAc, and the organic layer was concentrated. The residue was purified by silica gel column chromatography (eluting with PE/EtOAc v/v 2:1) to give N-methyl-8-nitroquinolin-7-amine as a yellow solid (1.6 g, yield 79%). ESI MS: m/z 204 [M+H]+.

Workup

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. extractionThe mixture was extracted with EtOAc
  3. concentrationthe organic layer was concentrated
  4. customThe residue was purified by silica gel column chromatography (
  5. washeluting with PE/EtOAc v/v 2:1)

Sources & evidence

ORD record
ord-a5574104e15c45fea88c47f82c713a9a
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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