Methylamine → N-Methyl-1-(quinolin-2-yl)methanamine

HRID 1091075Notes

Reaction equation

HRID 1091075 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:14][NH2:15]>O>[CH3:14][NH:15][CH2:3][C:4]1[CH:13]=[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 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 15675896N-Methyl-1-(quinolin-2-yl)methanamineYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloromethylquinoline hydrochloride (3.00 g, 14.01 mmol) was suspended in aqueous methylamine (40 mL, 40 wt % in H2O) at 10° C. under a N2 atmosphere. After 20 minutes, the reaction mixture was warmed to room temperature and stirred for 3 hours. The mixture was diluted with water and extracted with dichloromethane. The organic extracts were dried (MgSO4) and concentrated to afford 2.22 g (92%) of pure product as a brown oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7bc14c4ce28f40cab7c2874154765d56
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

Loading…