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

Reaction equation

[CH2:1]([P:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16].S(=O)(=O)(O)O.N>>[N+:15]([C:5]1[CH:6]=[CH:7][C:2]([CH2:1][P:8]2(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:3][CH:4]=1)([O-:17])=[O:16]

Participants

Reactant 4

HCID 222Ammonia

HCID 944Nitric Acid

HCID 1118Sulfuric Acid

HCID 184725391-Benzylphosphorinane-1-oxide

Product 1

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

Conditions

Temperature: 55 °C

Procedure

To 1-benzylphosphorinane-1-oxide (5.39 g) were added nitric acid (1.94 ml) and sulfuric acid (15 ml) at 0° C., and the mixture was stirred at 50-60° C. for 2 hours. The reaction mixture was added to crushed ice-water, neutralized with ammonia solution and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethanol/ethyl acetate=1:3→1:2) to give 1-(4-nitrobenzyl)phosphorinane-1-oxide (2.47 g) as pale yellow crystals.