Trimethyl phosphite → HCID 53679805, compound

HRID 726625Notes

Reaction equation

HRID 726625 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[P:14]([O:19]C)([O:17][CH3:18])[O:15][CH3:16]>C1(C)C=CC=CC=1>[CH3:16][O:15][P:14]([CH2:2][C:3]1[C:4]([CH3:13])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)([O:17][CH3:18])=[O:19]

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 19706749HCID 19706749, compound

Product 1

HCID 53679805HCID 53679805, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the obtained 3-bromomethyl-2-methylquinoline (0.25 g, 1.0 mmol) and trimethyl phosphite (0.4 ml, 3.2 mmol) was refluxed in toluene (10 ml) for 16 hours. The reaction mixture was then concentrated in vacuo and the residue was flash chromatographed on silica gel. Elution with ethyl acetate afforded 0.28 g of 3-(dimethylphosphonomethyl)-2-methylquinoline.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customchromatographed on silica gel
  3. washElution with ethyl acetate

Sources & evidence

ORD record
ord-167d73f1f10948d5b715482c30dea8e1
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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