Ethanol, 2-(4-amino-3-nitrophenoxy)- → 2-(3,4-Diaminophenoxy)ethanol

HRID 1777733Notes

Reaction equation

HRID 1777733 reaction equation
C([O-])=O.[NH4+].[NH2:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][OH:13])=[CH:8][C:7]=1[N+:16]([O-])=O>CO.O.[Pd]>[NH2:16][C:7]1[CH:8]=[C:9]([CH:14]=[CH:15][C:6]=1[NH2:5])[O:10][CH2:11][CH2:12][OH:13]

Participants

5

Reactant 2

HCID 148519Ethanol, 2-(4-amino-3-nitrophenoxy)-HCID 2723923Ammonium formate

Product 1

HCID 858556112-(3,4-Diaminophenoxy)ethanolYield 113.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22242641Methanol--water (1/1)Solvent

Procedure

A degassed solution of ammonium formate (1.4 g) in MeOH/water (10/1) was added to 2-(4-amino-3-nitrophenoxy)ethan-1-ol (234 mg), followed by Pd/C (10%). The flask was closed and the reaction mixture was stirred at RT for 20 h. The reaction mixture was filtered off and Pd/C was further washed with MeOH/water. The filtrate was lyophilized to afford 225 mg of black solid. 1H-NMR (DMSO): 8.19 (s, 1H); 6.41 (d, 1H, 8.3 Hz); 6.17 (d, 1H, 2.7 Hz); 5.98 (dd, 1H, 2.8 Hz and 8.3 Hz); 4.98 (br s, NH2); 3.77 (t, 2H, 5.2 Hz); 3.63 (t, 2H, 5 Hz).

Workup

  1. customThe flask was closed
  2. filtrationThe reaction mixture was filtered off
  3. washPd/C was further washed with MeOH/water

Sources & evidence

ORD record
ord-b23c4065c84a4ee6aa71f8ac3710f6d5
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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