Water → HCID 86699129, compound

HRID 1424217Notes

Reaction equation

HRID 1424217 reaction equation
[CH3:1][C:2]([C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[C:8]([N+:13]([O-])=O)[CH:7]=1)([CH3:5])[CH2:3][CH3:4].O.[Cl-].[Ca+2].[Cl-]>CCO.[Fe]>[CH3:5][C:2]([C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:10])=[CH:11][CH:12]=1)([CH3:1])[CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 86699130HCID 86699130, compound

Product 1

HCID 86699129HCID 86699129, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of 4-(1,1-dimethylpropyl)-2-nitroaniline (Preparation 94, 11 g, 0.052 mol) in EtOH:water (240 mL:60 mL) was added iron powder (14.8 g, 0.254 mol) and calcium chloride (11.7 g, 0.105 mol). The reaction was heated to reflux for 6 hours before cooling and concentrating in vacuo. The residue was extracted with EtOAc, dried over Na2SO4, concentrated in vacuo and purified using silica gel column chromatography eluting with 50% EtOAc in hexane to afford the title compound (6.2 g, 65%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 6 hours
  3. temperaturebefore cooling
  4. concentrationconcentrating in vacuo
  5. extractionThe residue was extracted with EtOAc
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. custompurified
  9. washeluting with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-1f55d7fb75834fceb9e2ba86c34e88df
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

Loading…