Phosphorus oxychloride → HCID 86614221, compound

HRID 2092349Notes

Reaction equation

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

Participants

Conditions

Temperature: 108 °C

Procedure

A suspension of 5-iodo-6-methylphthalazin-1(2H)-one (8.51 g, 29 7 mmol) in phosphorous oxychloride (200 ml, 2146 mmol), charged to a 500 mL was stirred at 108° C. (reflux) for 90 min. The POCl3 was then removed under vacuum, and the resulting residue was azeotroped 2× with toluene. The resulting residue was dissolved in a mixture of DCM and MeOH and water. The layers were separated the aqueous layer was washed with DCM 3×. The combined organics were washed with saturated aqueous sodium carbonate and brine. The organic layer was then dried over magnesium sulfate, and loaded on to silica. 1-Chloro-5-iodo-6-methylphthalazine (5.604 g, 61.9% yield) was obtained by column chromatography (ISCO 330 g 15%-60% EtOAc in Hex 60 min) as a yellow solid. MS (M+H)+ 305.

Workup

additioncharged to a 500 mL
temperature(reflux) for 90 min
customThe POCl3 was then removed under vacuum
customthe resulting residue was azeotroped 2× with toluene
dissolutionThe resulting residue was dissolved in a mixture of DCM and MeOH and water
customThe layers were separated the aqueous layer
washwas washed with DCM 3×
washThe combined organics were washed with saturated aqueous sodium carbonate and brine
dry with materialThe organic layer was then dried over magnesium sulfate

Sources & evidence

ORD record: ord-cfd5145b94e5482887bc64bbeca70c1d
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08440674B2

Reaction notes

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