8-Nitroquinoline → 3-Iodo-8-nitroquinoline

HRID 2116523Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].[I:14]N1C(=O)CCC1=O>C(O)(=O)C>[I:14][C:10]1[CH:11]=[N:12][C:13]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2]

Participants

Conditions

Temperature: 62 °C

Procedure

A stirred mixture of 8-nitroquinoline (100 g, 0.57 mol) in acetic acid (500 ml) was treated with N-iodosuccinimide (155 g, 0.69 mol) portionwise over 10 minutes, and warmed to 62° C. for 6 h. A further portion of N-iodosuccinimide (25 g, 0.14 mol) was introduced and the mixture stirred for a further 16 h before cooling to ambient temperature. The solvent was removed in vacuo, keeping the temperature below 35° C. The residue was dissolved in dichloromethane (2 L) and washed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulfate solution (1 L), water (1 L), brine (100 ml), then the organic phase was dried over magnesium sulfate. The mixture was filtered and the solvent removed to give a yellow solid which was recrystallised from ethyl acetate to give the title compound (D3) (168 g, 97%) as a yellow solid;

Workup

temperaturebefore cooling to ambient temperature
customThe solvent was removed in vacuo
customthe temperature below 35° C
dissolutionThe residue was dissolved in dichloromethane (2 L)
washwashed successively with saturated aqueous sodium bicarbonate solution (2×1 L), 10% aqueous sodium thiosulfate solution (1 L), water (1 L), brine (100 ml)
dry with materialthe organic phase was dried over magnesium sulfate
filtrationThe mixture was filtered
customthe solvent removed
customto give a yellow solid which
customwas recrystallised from ethyl acetate

Sources & evidence

ORD record: ord-aad67579209b45228db1aa9e8456da12
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439244B2

Reaction notes

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