Methylamine → 4-Methylamino-3-nitroquinoline

HRID 580523Notes

Reaction equation

HRID 580523 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][NH2:16]>C(O)C>[CH3:15][NH:16][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 139583214-Methylamino-3-nitroquinolineYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspension of 2.0 g of 4-chloro-3-nitroquinoline in 20 ml of dry ethanol is added 15 ml of 30% methylamine in ethanol. The mixture is stirred at room temperature for 30 minutes and concentrated in vacuo. The residue is triturated with excess water. The resulting crystals are collected by filtration and washed repeatedly with water. The crystals are dried over phosphorus pentoxide in vacuo to afford 1.82 g (93%) of 4-methylamino-3-nitroquinoline.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue is triturated with excess water
  3. filtrationThe resulting crystals are collected by filtration
  4. washwashed repeatedly with water
  5. dry with materialThe crystals are dried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-a0273dc5255247159c8d25faa317f8ae
Source dataset
uspto-grants-1988_06
Patent number
US04753951

Reaction notes

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