Ethyl Acetate → 2-Nitro-5-(3-diethylamino-1-propoxy)aniline

HRID 2054536

Reaction equation

HRID 2054536 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].C(=O)([O-])[O-].[NH4+:24].[NH4+].CCOC(C)=O>CN(C=O)C>[N+:17]([C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:7][C:2]=1[NH2:24])([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 517111Ammonium CarbonateHCID 220147332-Fluoro-4-(3-diethylamino-1-propoxy)nitrobenzene

Product 1

HCID 220147182-Nitro-5-(3-diethylamino-1-propoxy)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The nitro compound obtained as above (1.5 mmol) is dissolved in DMF (4 mL) and added with ammonium carbonate (500 mg). The reaction mixture is then heated at 80° C. for 48 h. EtOAc (2×10 mL). The combined organic layers are then washed with water and brine and dried over Na2SO4. Removal of the solvent in vacuo yielded the 2-nitro-5-(3-diethylamino-1-propoxy)aniline (300 mg) which is used for further transformation without any purification.

Workup

  1. washThe combined organic layers are then washed with water and brine
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-533bc1d78966435e9472b359c24e93b1
Source dataset
uspto-grants-2008_02
Patent number
US07329684B2

Linked notes

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