2-Methoxyethylamine → N-(2-Methoxyethyl)-2-nitroaniline

HRID 2293114Notes

Reaction equation

HRID 2293114 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][CH2:9][CH2:10][NH2:11].F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]>C1COCC1.C(OCC)(=O)C>[CH3:7][O:8][CH2:9][CH2:10][NH:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 80182-MethoxyethylamineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 10375425N-(2-Methoxyethyl)-2-nitroaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (4.15 g) and 2-methoxyethylamine (1.3 ml) were added to a solution of 1-fluoro-2-nitrobenzene (1.56 ml) in dry THF (20 ml). The mixture was stirred at 23° for 24 h, then it was diluted with ethyl acetate, washed with a saturated ammonium chloride solution (100 ml), 10% sodium hydroxide solution (100 ml) and brine (100 ml), dried and concentrated in vacuo. The residue was purified by flash chromatography (eluting with CH-EA 3:1) to give the title compound as an orange oil (2.55 g). T.l.c. CH-EA (2:1), Rf 0.51.

Workup

  1. washwashed with a saturated ammonium chloride solution (100 ml), 10% sodium hydroxide solution (100 ml) and brine (100 ml)
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography (eluting with CH-EA 3:1)

Sources & evidence

ORD record
ord-d0a61be6b5aa418a8231df719ee24436
Source dataset
uspto-grants-1997_11
Patent number
US05686449

Reaction notes

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