Ammonium Chloride → 3-(Dimethylphosphoryl)aniline

HRID 1026798Notes

Reaction equation

HRID 1026798 reaction equation
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([CH3:4])=[O:3].[Cl-].[NH4+]>CO.O.[Fe]>[CH3:4][P:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])([CH3:1])=[O:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 1902781-Dimethylphosphoryl-3-nitrobenzene

Product 1

HCID 582077813-(Dimethylphosphoryl)anilineYield 100.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of compound 286 (1.5 g, 7.5 mmol) in methanol (62 ml) and water (12 ml) under nitrogen at room temperature was added ammonium chloride (0.604 g, 11.3 mmol) and iron (1.68 g, 30.1 mmol). The resulting mixture was heated to reflux for 30 min then filtered through celite. The celite pad was rinsed with methanol. The filtrate and washings were combined and concentrated and the residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column) to afford compound 287 as a yellow solid (1.27 g, 7.51 mmol, quantitative). MS (m/z): 170.1 (M+H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationthen filtered through celite
  4. washThe celite pad was rinsed with methanol
  5. concentrationconcentrated
  6. customthe residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column)

Sources & evidence

ORD record
ord-b6b31f0c4aa248cca60720263415a555
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

Loading…