Phosphorus oxychloride → HCID 58466468, compound

HRID 1668957Notes

Reaction equation

HRID 1668957 reaction equation
[I:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=O.P(Cl)(Cl)([Cl:16])=O>>[Cl:16][C:7]1[C:8]2[C:3](=[C:2]([I:1])[C:11]([CH3:12])=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 44479177HCID 44479177, compound

Product 1

HCID 58466468HCID 58466468, compoundYield 93.9%

Conditions

Temperature
100 °C

Procedure

5-Iodo-6-methylisoquinolin-1(2H)-one (2.00 g, 7.02 mmol) was treated with phosphorous oxychloride (6.54 ml, 70.2 mmol) and the mixture stirred at 100° C. for 4 hours. The mixture was cooled and the volatiles removed in vacuo. The residue was taken up in DCM and washed twice with cold water and then twice with saturated aqueous sodium bicarbonate. The organic was dried with sodium sulfate, loaded unto silica and purified by column chromatography on silica gel using 20 to 60% EA in hexanes to give 1-chloro-5-iodo-6-methylisoquinoline (2.00 g, 93.9% yield) as a tan solid. MS (M+H)+ 303.7.

Workup

  1. temperatureThe mixture was cooled
  2. customthe volatiles removed in vacuo
  3. washwashed twice with cold water
  4. dry with materialThe organic was dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using 20 to 60% EA in hexanes

Sources & evidence

ORD record
ord-639daddec8a445758423377209bb10cd
Source dataset
uspto-grants-2011_08
Patent number
US07989461B2

Reaction notes

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