Phosphorus oxychloride → HCID 86683224, compound

HRID 1852154Notes

Reaction equation

[I:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5](O)=[N:4][CH:3]=1.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[C:2]([I:1])=[CH:3][N:4]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 178487750HCID 178487750, compound

Product 1

HCID 86683224HCID 86683224, compoundYield 61.2%

Conditions

Temperature: 0 °C

Procedure

A solution of 4-iodo-6-methoxyisoquinolin-1-ol (2 g, 6.64 mmol) in POCl3 (10 mL) was refluxed for 4 h. After concentration, the residue was taken into a mixture of 100 mL of DCM and 50 mL of water, cooled to 0° C., neutralized with 3 N NaOH, dried over MgSO4, concentrated and purified via silica gel chromatography (5-20% EtOAc:Hex) to give the pure product 1-chloro-4-iodo-6-methoxyisoquinoline (1.3 g, 4.07 mmol, 61.2% yield) as an orange solid. 1H NMR (400 MHz, DMSO-d6) δ 8.69 (s, 1H), 8.22 (d, J=9.3 Hz, 1H), 7.54 (dd, J=9.3, 2.5 Hz, 1H), 7.33 (d, J=2.5 Hz, 1H), 4.03 (s, 3H). MS: MS m/z 320(M++1).

Workup

concentrationAfter concentration
additionthe residue was taken into a mixture of 100 mL of DCM and 50 mL of water
dry with materialdried over MgSO4
concentrationconcentrated
custompurified via silica gel chromatography (5-20% EtOAc:Hex)

Sources & evidence

ORD record: ord-2def6e3e61a14010a5908f87348da777
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957203B2

Reaction notes

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