1-Methoxy-2-propanol → N,N'-Dimethyl-N-(2-methyl-4-quinolyl)ethane-1,2-diamine

HRID 333046

Reaction equation

HRID 333046 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[CH3:13][NH:14][CH2:15][CH2:16][NH:17][CH3:18].COCC(O)C>>[CH3:13][N:14]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1)[CH2:15][CH2:16][NH:17][CH3:18]

Participants

4

Reactant 3

HCID 79001-Methoxy-2-propanolHCID 8070N,N'-DimethylethylenediamineHCID 779734-Chloro-2-methylquinoline

Product 1

HCID 62593346N,N'-Dimethyl-N-(2-methyl-4-quinolyl)ethane-1,2-diamine

Conditions

Temperature
110 °C

Procedure

4-Chloroquinaldine (1.5 g, 5 mmol) was mixed with N,N′-dimethylethylenediamine (2.45 ml, 25 mmol) and 1-methoxy-2-propanol (8 ml) and stirred at 110° C. overnight. The mixture was purified by column chromatography (pre-packed silica column, gradient of heptane/ethyl acetate each containing 1% triethylamine). 0.4 g were obtained (1.75 mmol; 35%). MS (APCI) m/z=230.0 [M+H]+.

Workup

  1. customThe mixture was purified by column chromatography (pre-packed silica column, gradient of heptane/ethyl acetate each containing 1% triethylamine)
  2. custom0.4 g were obtained (1.75 mmol; 35%)

Sources & evidence

ORD record
ord-a4a93f8d61484b439d763712b480ab17
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Linked notes

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