Hydrochloric Acid → 4-(1-Ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochloride

HRID 472669Notes

Reaction equation

HRID 472669 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][P:6](=[O:18])([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[ClH:19].[H][H]>C(O)C.[Pd]>[ClH:19].[CH2:1]([N:3]1[CH2:4][CH2:5][P:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)(=[O:18])[CH2:7][CH2:8]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 674791721-Ethyl-4-(4-nitro-phenyl)-perhydro-1,4-azaphosphorine 4-oxideHCID 178418361HCID 178418361, compound

Product 1

HCID 674788444-(1-Ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

1-Ethyl-4-(4-nitro-phenyl)-perhydro-1,4-azaphosphorine 4-oxide (269.80 mg, 1.0058 mmol) dissolved in Ethanol (50 mL) and treated with palladium on carbon 10% (90:10, carbon black:Palladium, 30 mg, 2 mmol), 2.5 M of hydrogen chloride in ethanol (1.21 mL, 3.02 mmol) and 50 PSI of hydrogen gas. The mixture was shaken on a Parr apparatus for 5 hours. The mixture was degassed and backflushed with nitrogen. The mixture was filtered through a plug of diatomaceous earth and washed with ethanol. The filtrate was evaporated. 4-(1-ethyl-4-oxido-1,4-azaphosphinan-4-yl)aniline hydrochloride was isolated (401 mg, 145%). MS=238 (MH)+.

Workup

  1. customThe mixture was degassed
  2. filtrationThe mixture was filtered through a plug of diatomaceous earth
  3. washwashed with ethanol
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-01e74aac1b1842699b7ee42036a15008
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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