Methylamine → N-Methyl-1-(6-nitroquinolin-2-yl)methanamine

HRID 1091088Notes

Reaction equation

HRID 1091088 reaction equation
[CH3:1][NH2:2].Cl[CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=2)[N:6]=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][CH2:4][C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=2)[N:6]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 126651392-(Chloromethyl)-6-nitroquinoline

Product 1

HCID 15675909N-Methyl-1-(6-nitroquinolin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

Methylamine (g) was bubbled through a stirring solution of 2-(chloromethyl)-6-nitroquinoline (5.00 g, 22.47 mmol) in toluene (70 mL) at 0° C. The mixture was slowly warmed to 20° C. over 4 hours, concentrated to 1/2 volume, and partitioned between 10% aqueous K2CO3 /ethyl acetate. The organic phase was dried (MgSO4), decolorized (charcoal) and concentrated. Yield: 4.89 g as a brown solid which was used without purification.

Workup

  1. concentrationconcentrated to 1/2 volume
  2. custompartitioned between 10% aqueous K2CO3 /ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated
  5. customYield: 4.89 g as a brown solid which was used without purification

Sources & evidence

ORD record
ord-7484a992fcb048b994b9143c76443d51
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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