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

HRID 1277174Notes

Reaction equation

HRID 1277174 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

5

Reactant 4

HCID 222AmmoniaHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 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 2hours. 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.

Workup

  1. additionThe reaction mixture was added
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethanol/ethyl acetate=1:3→1:2)

Sources & evidence

ORD record
ord-7e204b14ebf144fc990f860b4e4640ae
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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