Stannous Chloride → Diethyl (3-aminophenyl)phosphonate

HRID 1947792Notes

Reaction equation

HRID 1947792 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl[Sn]Cl>CCO>[CH2:6]([O:5][P:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[CH:10]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

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-469406a6997e4e3d962cc786b0992292
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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