Methylamine → HCID 20061012, compound

HRID 1085164Notes

Reaction equation

HRID 1085164 reaction equation
[CH3:1][NH2:2].Cl[C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1>C(O)C>[CH3:1][NH:2][C:4]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 126639372-Chloro-3-nitroquinoline

Product 1

HCID 20061012HCID 20061012, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Gaseous methylamine was bubbled through a suspension of 2-chloro-3-nitroquinoline (1.06 g, 5.1 mmol) in ethanol (20 ml) at 0° C. for 15 minutes. The solvent was removed under reduced pressure and the bright red residue was dissolved in dichloromethane (100 ml) and washed with saturated aqueous sodium bicarbonate (50 ml). The organic layer was dried (MgSO4) and concentrated under reduced pressure to give 2-methylamino-3-nitroquinoline (940 mg, 91%) as a red solid, m.p. 160° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe bright red residue was dissolved in dichloromethane (100 ml)
  3. washwashed with saturated aqueous sodium bicarbonate (50 ml)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bc4ee7d50e5f4ba080df8774900f8052
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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