1-(4-Nitrobenzyl)phosphorinane-1-oxide → 1-(4-Aminobenzyl)phosphorinane-1-oxide

HRID 1387929Notes

Reaction equation

HRID 1387929 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][P:9]2(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][P:9]2(=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 184722241-(4-Nitrobenzyl)phosphorinane-1-oxide

Product 1

HCID 229899861-(4-Aminobenzyl)phosphorinane-1-oxideYield 75.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-(4-nitrobenzyl)phosphorinane-1-oxide (2.25 g) and 10% Pd—C (0.2 g) in ethanol (30 ml) was vigorously stirred under hydrogen atmosphere for 24 hours. The catalyst was filtered off, and the filtrate was concentrated recrystallized from ethanol-diethylether to give 1-(4-aminobenzyl)-phosphorinane-1-oxide (1.5 g) as pale yellow crystals.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customrecrystallized from ethanol-diethylether

Sources & evidence

ORD record
ord-e33970d97fe947f293dd9a220a15e84e
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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