Iodine → HCID 21106352, compound

HRID 855937Notes

Reaction equation

[I:1]I.[N+:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH2:9]2)([O-:5])=[O:4]>CN(C)C=O.C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[I:1][C:13]1[CH:14]=[C:6]([N+:3]([O-:5])=[O:4])[CH:7]=[C:8]2[C:12]=1[NH:11][CH2:10][CH2:9]2

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of silver sulfate (100 g, 0.32 mol) and iodine (82 g, 0.32 mol) in N,N-dimethylformamide (700 mL) and ethanol (1400 mL) was treated with 5-nitro-2,3-dihydro-1H-indole I (48 g, 0.29 mol). The resulting mixture was stirred at 25° C. for 1.5 h, filtered and the filter pad washed with ethyl acetate. The filtrate was concentrated in vacuo to a volume of approximately 500 mL. This solution was treated with a 1.0N aqueous sodium thiosulfate solution (100 mL) and a saturated aqueous sodium chloride solution (400 mL). The resulting precipitate was collected by filtration, washed with water and petroleum ether, and dried in vacuo to afford 7-iodo-5-nitro-2,3-dihydro-1H-indole II (83.9 g, 98.9%) as a white solid: 1H NMR (DMSO-d6, 300 MHz) δ 8.18 (d, J=2.20 Hz, 1H), 7.80 (d, J=1.46 Hz, 1H), 7.03 (broad s, 1H) 3.65 (t, J=8.97 Hz, 2H), 3.17 (t, J=8.60 Hz, 2H).

Workup

filtrationfiltered
washthe filter pad washed with ethyl acetate
concentrationThe filtrate was concentrated in vacuo to a volume of approximately 500 mL
additionThis solution was treated with a 1.0N aqueous sodium thiosulfate solution (100 mL)
filtrationThe resulting precipitate was collected by filtration
washwashed with water and petroleum ether
customdried in vacuo

Sources & evidence

ORD record: ord-477b381576ad40a8aa444b82cec92396
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262297B2

Reaction notes

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