Triethylamine → 2-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamine

HRID 32368

Reaction equation

HRID 32368 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].C(N(CC)CC)C.[NH2:22][CH2:23][C:24]([NH2:27])([CH3:26])[CH3:25]>C(Cl)Cl.C(Cl)(Cl)Cl>[CH3:25][C:24]([NH2:27])([CH3:26])[CH2:23][NH:22][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

6

Reactant 3

HCID 8471TriethylamineHCID 131282-MethylpropylenediamineHCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 590266622-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamineYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-chloro-3-nitroquinoline (17.3 g, 83.2 mmol) in 200 mL of anhydrous CH2Cl2, under N2, was treated with triethylamine (23.2 mL, 166.4 mmol) and 1,2-diamino-2-methylpropane (9.57 mL, 91.5 mmol). After stirring overnight, the reaction mixture was diluted with 800 mL of CHCl3 washed with H2O (3×300 mL) and brine (300 mL). The organic portion was dried over Na2SO4 and concentrated to give 2-methyl-N1-(3-nitroquinolin-4-yl)propane-1,2-diamine (21.0 g) as a bright yellow solid.

Workup

  1. washwashed with H2O (3×300 mL) and brine (300 mL)
  2. dry with materialThe organic portion was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-57c77ad796b54a78af64277c0d7063d5
Source dataset
uspto-grants-2008_09
Patent number
US07427629B2

Linked notes

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