Stannous Chloride → Diethyl (3-aminophenyl)phosphonate

HRID 511219Notes

Reaction equation

HRID 511219 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl[Sn]Cl>CCO>[NH2:1][C:4]1[CH:5]=[C:6]([P:10](=[O:17])([O:11][CH2:12][CH3:13])[O:14][CH2:15][CH3:16])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 11737034HCID 11737034, compound

Product 1

HCID 284866Diethyl (3-aminophenyl)phosphonateYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of diethyl (3-nitrophenyl)phosphonate (520 mg, 2.0 mmol) and SnCl2 (1.8 g, 8 mmol) in EtOH (50 mL) was heated at reflux for 12 h. The mixture was then filtered and the filtrate concentrated in vacuo to yield a crude product, which was purified by preparative HPLC to afford 320 mg of desired diethyl (3-aminophenyl)phosphonate (yield: 69%).

Workup

  1. temperatureat reflux for 12 h
  2. filtrationThe mixture was then filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customto yield a crude product, which
  5. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-69a09e0fb9264d17961e75600bda41d4
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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