HCID 67060801, compound → HCID 70664257, compound

HRID 1186079Notes

Reaction equation

HRID 1186079 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([CH:19]=1)[NH:7][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>[Fe].O>[Br:1][C:2]1[CH:19]=[C:6]([NH:7][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:17])([CH3:16])[CH3:18])([CH3:13])[CH3:14])[C:5]([NH2:20])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67060801HCID 67060801, compound

Product 1

HCID 70664257HCID 70664257, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Bromo-N-(3-((tert-butyldimethylsilyl)oxy)propyl)-2-nitroaniline from above was added to 2:1 2-propanaol:water (75 mL) (precipitate formed). Iron powder was added (1.147 g, 20.6 mmol) and the mixture was heated to 80° C. for 1 h. It turned black. After allowing to cool, the mixture was filtered through celite, rinsing with ethyl acetate. The filtrate was washed with water, washed with then brine, dried (MgSO4), filtered, and concentrated to give crude 5-bromo-N1-(3-((tert-butyldimethylsilyl)oxy)propyl)benzene-1,2-diamine.

Workup

  1. temperatureto cool
  2. filtrationthe mixture was filtered through celite
  3. washrinsing with ethyl acetate
  4. washThe filtrate was washed with water
  5. washwashed with then brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bb2c330cf91d4166ac1c55b304c9c1f2
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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