Isopropanol → HCID 19977767, compound

HRID 2216083Notes

Reaction equation

HRID 2216083 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1C(=O)C2C(=CC=CC=2)C1=O)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].CC(O)C.NN>C1COCC1>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH2:14])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 9321HydrazineHCID 256579HCID 256579, compound

Product 1

HCID 19977767HCID 19977767, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pentyl]-phosphonic acid diethyl ester (0.300 g, 0.849 mmol) was dissolved in THF [2 mL], IPA [4 mL]. Hydrazine (0.081 g, 2.540 mmol) was added to this solution and stirred at room temperature for 18 hours. The white precipitate was filtered and washed with dichloromethane. Removal of the solvent in vacuo yielded the title compound (0.136 g, 72%) 1H-NMR (CDCl3): δ 4.07 (m, 4H), 2.68 (t, 2H, J=6.74 Hz), 1.72 (m, 2H), 1.60 (m, 2H), 1.43 (m, 4H), 1.31 (m, 6H).

Workup

  1. filtrationThe white precipitate was filtered
  2. washwashed with dichloromethane
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-73af12cfcc554a9887a6655ad12d5ab3
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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