Triethylamine → N2-(2-Methoxyethyl)-N2-methyl-5-nitropyridine-2,4-diamine

HRID 541197Notes

Reaction equation

HRID 541197 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.C(N(CC)CC)C.[CH3:19][O:20][CH2:21][CH2:22][NH:23][CH3:24]>CN(C=O)C.O>[CH3:19][O:20][CH2:21][CH2:22][N:23]([CH3:24])[C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 300977(2-Methoxyethyl)(methyl)amineHCID 109100582-Chloro-5-nitropyridin-4-amine

Product 1

HCID 68352493N2-(2-Methoxyethyl)-N2-methyl-5-nitropyridine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-5-nitropyridin-4-amine (500 mg, 2.88 mmol, 1.00 equiv), triethylamine (1.167 g, 11.53 mmol, 4.00 equiv), and (2-methoxyethyl)(methyl)amine (514 mg, 5.77 mmol, 2.00 equiv) in DMF (20 mL) was stiffed in a sealed tube at 55° C. behind a blast shield overnight. After cooling to room temperature, the mixture was diluted with 100 mL of water and extracted with 3×150 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to yield 723 mg (crude) of the title compound as a dark red oil.

Workup

  1. extractionextracted with 3×150 mL of ethyl acetate
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4659f5ac85a49c19b7aebdad49a664f
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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