Potassium Carbonate → 1-(3-Methoxy-4-nitrophenyl)-4-methyl-1,4-azaphosphinane 4-oxide

HRID 1472011Notes

Reaction equation

HRID 1472011 reaction equation
[CH3:1][P:2]1(=[O:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.F[C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([O:16][CH3:17])[CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:17][O:16][C:14]1[CH:15]=[C:10]([N:5]2[CH2:6][CH2:7][P:2](=[O:8])([CH3:1])[CH2:3][CH2:4]2)[CH:11]=[CH:12][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27792505-Fluoro-2-nitroanisoleHCID 552988994-Methyl-1,4lambda5-azaphosphinan-4-one

Product 1

HCID 681569881-(3-Methoxy-4-nitrophenyl)-4-methyl-1,4-azaphosphinane 4-oxideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-methyl-[1,4]azaphosphinane-4-oxide (133 mg, 1.00 mmol), 5-fluoro-2-nitroanisole (340 mg, 2.00 mmol), K2CO3 (345 mg, 2.50 mmol), and DMF (5 mL) was heated to 50° C. After 2 h, the reaction mixture was concentrated and purified by silica gel chromatography (0-5% 7N ammonia in methanol:dichloromethane) to afford 1-(3-methoxy-4-nitrophenyl)-4-methyl-1,4-azaphosphinane 4-oxide as a bright yellow solid (272 mg, 96% yield).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by silica gel chromatography (0-5% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-473d397c0ff7461ba7c5e85bb4b6b393
Source dataset
uspto-grants-2015_04
Patent number
US09012462B2

Reaction notes

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