Hydrazine hydrate (1:1) → 3-Methoxytyramine

HRID 2112299Notes

Reaction equation

HRID 2112299 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][N+:11]([O-])=O)[CH:6]=[CH:5][C:4]=1[OH:14].O.NN>C(O)C.[Ni]>[NH2:11][CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][C:4]([OH:14])=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 230726552-Methoxy-4-(2-nitroethyl)phenol

Product 1

HCID 16693-Methoxytyramine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 2-methoxy-4-(2-nitro-ethyl)-phenol (2.0 g) and Raney-nickel (3.7 g) in ethanol (30 ml) is added hydrazine hydrate (3.8 g) during 30 minutes. The reaction mixture is stirred for 1 hour at room temperature. After filtration the reaction mixture is poured into water (350 ml). It is extracted with ethyl acetate (2×400 ml) washed with brine (2×50 ml) dried (Na2SO4) and evaporated. 4-(2-amino-ethyl)-2-methoxy-phenol is obtained as colorless crystals.

Workup

  1. filtrationAfter filtration the reaction mixture
  2. additionis poured into water (350 ml)
  3. extractionIt is extracted with ethyl acetate (2×400 ml)
  4. washwashed with brine (2×50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-f2fa24f250764f1893878e2b5d549f16
Source dataset
uspto-grants-2009_04
Patent number
US07521579B2

Reaction notes

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