Toluene → Diisopropyl alpha-(4-hydroxy-3-methoxy-5-methylphenyl)-N-methyl-N-(3-picolyl)-aminomethylphosphonate

HRID 431446Notes

Reaction equation

HRID 431446 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=O)=[CH:4][C:3]=1[O:11][CH3:12].C[NH:14][CH2:15][C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[P:22]([O-:31])([O:27][CH:28]([CH3:30])[CH3:29])[O:23][CH:24]([CH3:26])[CH3:25].[C:32]1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]2[C:20]([CH2:19][N:18]([CH2:17][P:22](=[O:31])([O:27][CH:28]([CH3:30])[CH3:29])[O:23][CH:24]([CH3:26])[CH3:25])[CH3:32])=[CH:21][CH:16]=[CH:15][N:14]=2)=[CH:4][C:3]=1[O:11][CH3:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 883933-(Methylaminomethyl)pyridineHCID 14878064-Hydroxy-3-methoxy-5-methylbenzaldehydeHCID 21884976Phosphorous acid, bis(1-methylethyl) ester

Product 1

HCID 136404658Diisopropyl alpha-(4-hydroxy-3-methoxy-5-methylphenyl)-N-methyl-N-(3-picolyl)-aminomethylphosphonateYield 40%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

A mixture of 2.0 g (12 mmol) of 4-hydroxy-3-methoxy-5-methylbenzaldehyde, 1.8 g (13.2 mmol) of N-methyl-3-picolylamine and 2.2 g (13.2 mmol) diisopropyl phosphite dissolved in 15 ml toluene and a catalytic amount of p-toluenesulfonic acid (ca. 2 mg) contained in a flask connected to a Dean Stark apparatus was refluxed for 2 h. The solution was evaporated and the residue was purified by column chromatography (95/5 CHCl3/MeOH) to yield 2.1 g (40%) of a yellow oil.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe solution was evaporated
  3. customthe residue was purified by column chromatography (95/5 CHCl3/MeOH)

Sources & evidence

ORD record
ord-a500614fa3f94262919079f6ebee0c1f
Source dataset
uspto-grants-2003_12
Patent number
US06660724B1

Reaction notes

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