N,N-Diethyl-3-fluoro-4-nitrobenzamide → 3-Amino-N,N-diethyl-4-nitrobenzamide

HRID 1796503Notes

Reaction equation

HRID 1796503 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7](F)[CH:6]=1)[CH3:2].[NH4+:18].[OH-].CCO>>[NH2:18][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12])[C:4]([N:3]([CH2:16][CH3:17])[CH2:1][CH3:2])=[O:15]

Participants

3

Reactant 2

HCID 22181417N,N-Diethyl-3-fluoro-4-nitrobenzamideHCID 22731726Ethanol ammonium hydroxide

Product 1

HCID 221814143-Amino-N,N-diethyl-4-nitrobenzamideYield 86%

Procedure

N,N-Diethyl-3-fluoro-4-nitro-benzamide (5.1 g, 21.2 mmol) was refluxed in a 2:1 mixture of NH4OH/EtOH (150 mL) for 48 h. The solution was cooled to rt and the solvent concentrated. The solution was then extracted (3×) with EtOAc. The combined organic phases were washed with brine and dried over anhydrous MgSO4. The crude product was crystallized from EtOAc/hexanes to give the title compound (4.35 g, 86% yield). 1H NMR (400 MHz, CD3OD) δ 8.12 (d, J=8.8 Hz, 1H), 6.92 (s, 1H), 6.56 (d, J=8.8 Hz, 1H), 3.51 (q, J=7.2 Hz, 2H), 3.28 (m, 2H), 1.23 (t, J=7.2 Hz, 3H), 1.13 (t, J=7.2 Hz, 3H).

Workup

  1. concentrationthe solvent concentrated
  2. extractionThe solution was then extracted (3×) with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe crude product was crystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-7be7dcbf130b40f29d8c70de9986ea06
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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