Bis(2-Methoxyethyl)amine → 4-[Bis(2-methoxyethyl)amino]-3-nitrobenzoic acid

HRID 1950820Notes

Reaction equation

HRID 1950820 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][O:8][CH3:9].F[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]>CCO>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:6][CH2:7][O:8][CH3:9])[C:11]1[CH:19]=[CH:18][C:14]([C:15]([OH:17])=[O:16])=[CH:13][C:12]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 2383Bis(2-Methoxyethyl)amineHCID 679874-Fluoro-3-nitrobenzoic acid

Product 1

HCID 596065384-[Bis(2-methoxyethyl)amino]-3-nitrobenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bis(2-methoxyethyl)amine (Aldrich B4,820-7; 1.6 g; 12 mmol; 3 eq.) was added to a solution of 4-fluoro-3-nitrobenzoic acid (740 mg; 4 mmol; 1 eq.) in EtOH (20 mL) and the resulting mixture was stirred at room temperature for 2 hours then at 70° C. for 20 hours. The solution was concentrated in vacuo and the residue was partitioned between NaOH 0.5M and Et2O. The aqueous layer was acidified to pH 2 with HCl 5M, extracted with ethyl acetate (3×) and the combined organic phase was dried over magnesium sulfate. After evaporation of the solvent, the residue was crystallised from ethyl acetate/n-pentane to afford the title compound (1.12 g, 94%) as a yellow solid.

Workup

  1. waitat 70° C. for 20 hours
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between NaOH 0.5M and Et2O
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialthe combined organic phase was dried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was crystallised from ethyl acetate/n-pentane

Sources & evidence

ORD record
ord-59fb7e3b3bd1465489bd46d742db6d35
Source dataset
uspto-grants-2013_03
Patent number
US08404676B2

Reaction notes

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