Hydrazine hydrate (1:1) → Diethyl (2-aminoethyl)phosphonate

HRID 870128Notes

Reaction equation

HRID 870128 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][P:14](=[O:21])([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17].O.NN>C(O)C>[NH2:3][CH2:12][CH2:13][P:14](=[O:21])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 2543772-(2-Diethoxyphosphorylethyl)isoindole-1,3-dione

Product 1

HCID 2733596Diethyl (2-aminoethyl)phosphonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of diethyl 2-(1,3-dioxoisoindolin-2-yl)ethylphosphonate (5 g, 16.08 mmol, 1.00 equiv) in ethanol (200 mL) and hydrazine hydrate (8 g, 160.00 mmol, 9.95 equiv). The resulting solution was stirred for 12 h at room temperature. The solids were filtered and the resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with dichloromethane/methanol (9:1). This resulted in 1.5 g (51%) of diethyl 2-aminoethylphosphonate as colorless oil.

Workup

  1. customInto a 500-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. filtrationThe solids were filtered
  4. concentrationthe resulting mixture was concentrated under vacuum
  5. washeluted with dichloromethane/methanol (9:1)
  6. customThis resulted in 1.5 g (51%) of diethyl 2-aminoethylphosphonate as colorless oil

Sources & evidence

ORD record
ord-1eaef9a234904e858ce7d6cf3b553aed
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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