Methanol → N-Ethyl-2-nitroaniline

HRID 2110389Notes

Reaction equation

HRID 2110389 reaction equation
[CH2:1]([NH2:3])[CH3:2].CO.F[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]>>[CH2:1]([NH:3][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 6341EthylamineHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 82354N-Ethyl-2-nitroaniline

Conditions

Temperature
55 °C

Procedure

To a solution of ethylamine in methanol (2.0 M, 150 mL, 300 mmol) was added 1-fluoro-2-nitrobenzene (8 mL, 75.7 mmol). The reaction mixture was placed in a sealed vessel and heated to 55° C. for 15 hours. The solvent was removed in vacuo and the residue was taken up in ethyl acetate (200 mL), washed with a saturated aqueous solution of sodium bicarbonate (80 mL), and dried over anhydrous sodium sulfate (50 g). After removal of solvent, ethyl-(2-nitro-phenyl)-amine (12.5 g, 75 mmol) was obtained as a brown oil. MS (ES) m/z 167.1.

Workup

  1. customThe reaction mixture was placed in a sealed vessel
  2. customThe solvent was removed in vacuo
  3. washwashed with a saturated aqueous solution of sodium bicarbonate (80 mL)
  4. dry with materialdried over anhydrous sodium sulfate (50 g)
  5. customAfter removal of solvent

Sources & evidence

ORD record
ord-3842e1041cd44a44b62d0f5d9a7bfaec
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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