Acetic Acid → 4-((tert-Butyldimethylsilyl)oxy)benzene-1,2-diamine

HRID 920117Notes

Reaction equation

HRID 920117 reaction equation
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([N+:16]([O-])=O)[CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(=O)C>CCO.[Fe]>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:16])[C:12]([NH2:15])=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 120422994-(Tert-butyldimethylsilyl)oxy-2-nitroaniline

Product 1

HCID 672786584-((tert-Butyldimethylsilyl)oxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The mixture of 4-(tert-butyldimethylsilyloxy)-2-nitrobenzenamine (0.5 g, 1.9 mmol), Fe powder (1.1 g, 19 mmol) and acetic acid (1.0 mL, 18 mmol) in EtOH (10 mL) was stirred at reflux for 4 hrs. The mixture was filtered through celite pad and the filtrate was concentrated.

Workup

  1. temperatureat reflux for 4 hrs
  2. filtrationThe mixture was filtered through celite pad
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-64301a4e86764faaa072ab461b72ee38
Source dataset
uspto-grants-2016_03
Patent number
US09273046B2

Reaction notes

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