Trimethyl phosphite → HCID 54514340, compound

HRID 726629Notes

Reaction equation

HRID 726629 reaction equation
Br[CH2:2][C:3]1[C:4]([CH3:14])=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([Cl:13])=[CH:8][CH:7]=2.[P:15]([O:20]C)([O:18][CH3:19])[O:16][CH3:17]>C1(C)C=CC=CC=1>[Cl:13][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([CH3:14])[C:3]([CH2:2][P:15]([O:18][CH3:19])([O:16][CH3:17])=[O:20])=[CH:12]2

Participants

4

Reactant 2

HCID 8472Trimethyl phosphiteHCID 19706754HCID 19706754, compound

Product 1

HCID 54514340HCID 54514340, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3-bromomethyl-6-chloro-2-methylquinoline (0.85 g, 3.0 mmol) and trimethyl phosphite (1.2 ml, 9.6 mmol) was refluxed in toluene (20 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 0.90 g of 6-chloro-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-fef23e83a9b941bc985afc890093a8b3
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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