2-Methoxyethylamine → 3-bromo-N-(2-methoxyethyl)-5-nitropyridin-2-amine

HRID 340471Notes

Reaction equation

HRID 340471 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][CH2:10][CH2:11][NH2:12].O1CCCC1.[Br:18][C:19]1[C:20](Cl)=[N:21][CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1>O>[Br:18][C:19]1[C:20]([NH:12][CH2:11][CH2:10][O:9][CH3:8])=[N:21][CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=1

Participants

6

Reactant 4

HCID 80182-MethoxyethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 795353203-bromo-N-(2-methoxyethyl)-5-nitropyridin-2-amineYield 134%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine (53 μl) and 2-methoxyethylamine (23 mg) were added to a tetrahydrofuran (2 ml) solution containing 3-bromo-2-chloro-5-nitropyridine (60 mg), followed by stirring at room temperature for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=6:1 to 3:1), and a light yellow solid of 3-bromo-N-(2-methoxyethyl)-5-nitropyridin-2-amine (93.5 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=6:1 to 3:1)

Sources & evidence

ORD record
ord-6bacd450bdf6420f91e663be831853fd
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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