Ammonium Chloride → 3-(Dimethylphosphoryl)aniline

HRID 409957Notes

Reaction equation

HRID 409957 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-28bb42a3a65344309b891ef14b6857dd
Source dataset
uspto-grants-2014_06
Patent number
US08759522B2

Reaction notes

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