Hydrazine hydrate (1:1) → 1-(4-Amino-phenoxy)-3-diethylaminopropan-2-ol

HRID 2352875Notes

Reaction equation

HRID 2352875 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[CH2:4][CH:5]([OH:17])[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)[CH3:2].O.NN>C(O)C.[Ni]>[NH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:7][CH2:6][CH:5]([OH:17])[CH2:4][N:3]([CH2:1][CH3:2])[CH2:18][CH3:19])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 150724871-Diethylamino-3-(4-nitro-phenoxy)-propan-2-ol

Product 1

HCID 150725021-(4-Amino-phenoxy)-3-diethylaminopropan-2-olYield 99.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1-diethylamino-3-(4-nitro-phenoxy)-propan-2-ol (2.41 g, 8.99 mmol) in absolute ethanol (60 mL) was heated to 50° C. To the resulting solution was added hydrazine monohydrate (2.62 mL, 6 equiv.) followed by addition of a small portion of Raney nickel. The reaction mixture was heated at 50° C. with stirring for 1 h at which point all gas evolution had ceased. The reaction mixture was filtered through celite to remove the Raney nickel. The filtrate was concentrated in vacuo to give the 1-(4-Amino-phenoxy)-3-diethylaminopropan-2-ol as a light yellow oil (2.13 g).

Workup

  1. temperatureThe reaction mixture was heated at 50° C.
  2. filtrationThe reaction mixture was filtered through celite
  3. customto remove the Raney nickel
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-affdf3c07f714646a46f8fa7c37d7cbb
Source dataset
uspto-grants-2010_07
Patent number
US07749530B2

Reaction notes

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