Ethylamine → 2-(Ethylamino)-4-(3-diethylamino-1-propoxy)nitrobenzene

HRID 8053

Reaction equation

HRID 8053 reaction equation
F[C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[CH2:20]([NH2:22])[CH3:21]>C1COCC1>[CH2:20]([NH:22][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:5]=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18])[CH3:21]

Participants

4

Reactant 2

HCID 6341EthylamineHCID 220147332-Fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene

Product 1

HCID 220147352-(Ethylamino)-4-(3-diethylamino-1-propoxy)nitrobenzeneYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene (2 mmol; preparation described in Example 5) in THF (5 mL) is treated with ethylamine (4 mmol) at rt. After completion of the reaction, the reaction mixture is concentrated in vacuo. The residue is redissolved in EtOAc (10 mL), washed with saturated sodium bicarbonate solution, water, and brine. The organic phase is then dried over sodium sulfate and the solvent is removed in vacuo to afford the product, 2-(ethylamino)-4-(3-diethylamino-1-propoxy)nitrobenzene (520 mg) which was used for further transformation without further purification.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. dissolutionThe residue is redissolved in EtOAc (10 mL)
  4. washwashed with saturated sodium bicarbonate solution, water, and brine
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-8387d2f954384bf0b74112334218b3c6
Source dataset
uspto-grants-2006_08
Patent number
US07087632B2

Linked notes

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