Iodine → 8-chloro-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one

HRID 1398458Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1.OS(O)(=O)=O.[I:24](O)(=O)(=O)=O.II>C(O)(=O)C>[Cl:1][C:2]1[C:3]([I:24])=[CH:4][C:5]2[C:14]3[C:9](=[C:10]([CH3:15])[N:11]=[CH:12][CH:13]=3)[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 8-chloro-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.0 g, 3.87 mmol) in acetic Acid (25 mL) was added H2SO4 (0.206 mL, 3.87 mmol) followed by periodic acid (0.881 g, 3.87 mmol). The mixture was then heated to 80° C. for 20 min. I2 (0.294 g, 1.160 mmol) was then added at 80° C. and stirred for 120 min. After cooling to ambient temperature, the acetic acid was removed under reduced pressure. The residue was neutralized with 70 mL of saturated aqueous sodium bicarbonate solution. The solid so obtained was collected by vacuum filtration and air dried to afford 8-chloro-9-iodo-4,6-dimethylbenzo[c][2,7]naphthyridin-5(6H)-one (1.3 g, 3.21 mmol, 83% yield) as a brown solid. LC/MS (ESI) m/e 385.1 [(M+H)+, calcd for C14H11ClIN2O 384.9]; LC/MS retention time (method E): tR=1.09 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.96 (s, 1H) 8.69 (d, J=5.58 Hz, 1H) 8.36 (d, J=5.52 Hz, 1H) 7.76 (s, 1H) 3.63 (s, 3H) 3.00 (s, 3H).

Workup

temperatureAfter cooling to ambient temperature
customthe acetic acid was removed under reduced pressure
customThe solid so obtained
filtrationwas collected by vacuum filtration and air
customdried

Sources & evidence

ORD record: ord-c4577beb30e946abb03bb53dc8ba719e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901305B2

Reaction notes

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