4-Nitrophenol → N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

HRID 2392638Notes

Reaction equation

HRID 2392638 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][OH:37].[N+:39]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)([O-:41])=[O:40]>>[CH3:32][N:33]([CH2:34][CH2:35][CH2:36][O:37][C:45]1[CH:46]=[CH:47][C:42]([N+:39]([O-:41])=[O:40])=[CH:43][CH:44]=1)[CH3:38]

Participants

5

Reactant 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 766463-(Dimethylamino)-1-propanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 10353575N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amineYield 50%

Procedure

A stirred solution of diethyl azodicarboxylate (4.6 ml, 0.029 mole) and triphenylphosphine (7.60 g, 0.029 mole) in dry TBF (100 ml) was cooled to 0° C. 3-(Dimethylamino)propanol (3.43 ml, 0.029 mole) was added, followed by 4-nitrophenol (4.0 g, 0.029 mole) and the reaction mixture was stirred for 18 h at room temperature. The solvent was removed in vacuo, and the residue partitioned between 5N HCl and ethyl acetate. The aqueous layer was basified with 10% NaOH solution and extracted into ethyl acetate, dried (MgSO4) and evaporated in vacuo to leave the title compound as a yellow oil (3.2 g, 50%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between 5N HCl and ethyl acetate
  3. extractionextracted into ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-6d11a17efc5c453f894e403e26492d43
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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