Methylhydrazine → HCID 58989965, compound

HRID 1663106Notes

Reaction equation

HRID 1663106 reaction equation
[CH2:1]([O:6][C:7]1[CH:25]=[CH:24][C:10]([CH2:11][O:12][N:13]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].CNN>ClCCl>[CH2:1]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:11][O:12][NH2:13])=[CH:24][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 67132105HCID 67132105, compound

Product 1

HCID 58989965HCID 58989965, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution N-hydroxyphthalimide (2.45 g), 4-pentyloxybenzyl alcohol (Aldrich, 2.92 g) and triphenylphosphine (4.72 g) in THF was added drop-wise diethyl azodicarboxylate (1.2 eq.). The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (petroleum ether/EtOAc, 1/2, v/v) and gave 2-(4-pentyloxy-benzyloxy)-isoindole-1,3-dione. This phthalimide intermediate (4.35 g) was dissolved in dichloromethane and methyl-hydrazine (1.1 eq.) was added. The reaction mixture stirred at room temperature for 60 minutes and the formed solid material was removed by filtration. The filtrate was evaporated under reduced pressure and the residue was subjected to column chromatography on silica gel (petroleum ether/EtOAc, 5/1, v/v), and gave the title compound (2.55 g). 13C-NMR (CDCl3) δ 159.1, 130.1, 129.2, 114.5, 77.7, 68.0, 29.0, 28.2, 22.5, 14.0.

Workup

  1. customthe formed solid material was removed by filtration
  2. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3785883279ba4f14aa38218e55a39bb4
Source dataset
uspto-grants-2011_10
Patent number
US08034811B2

Reaction notes

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