2-(4-Amino-3-nitrophenoxy)ethyl bromide → 2-(3,4-Diaminophenoxy)ethyl bromide

HRID 1955232Notes

Reaction equation

HRID 1955232 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([O:6][CH2:7][CH2:8][Br:9])=[CH:4][C:3]=1[N+:12]([O-])=O>CCO>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[NH2:1])[O:6][CH2:7][CH2:8][Br:9]

Participants

3

Reactant 1

HCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Product 1

HCID 232945062-(3,4-Diaminophenoxy)ethyl bromideYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

From a mixture of 2-(4-amino-3-nitrophenoxy)ethyl bromide (1.30 g, 5.0 mmol) and stannouschloride dihydrate (5.65 g, 25 mmol) in 95% EtOH (35 mL) was obtained 960 mg (83%) of 2-(3,4-diaminophenoxy)ethyl bromide as a pale powder. 1H NMR (CDCl3): 3.597 (t, 2H, J=6), 4.210 (t, 2H, J=6), 6.273 (dd, 1H, J=8; 3), 6.359 (d, 1H, J=3), 6.637 (d, 1H, J=8).

Sources & evidence

ORD record
ord-de7da32cfd11478584a1a38027afe182
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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