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

HRID 8050
Notes
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Reaction equation

HRID 8050 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-2376017b04d24493a40d98ac5b74b779
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07087632B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes