Water → HCID 57765303, compound

HRID 2061849Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C(=O)([O-])[O-].[K+].[K+].I[CH2:26][CH2:27][OH:28].O>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[C:4]([I:18])[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:26][CH2:27][OH:28])[CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17]

Participants

Conditions

Temperature: 90 °C

Procedure

Ethyl 8-fluoro-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 11, 7.22 g, 20 mmol) was dissolved in dimethylformamide (35 ml). Powdered potassium carbonate (8.28 g, 60 mmol) and 2-iodoethanol (11.3 ml, 145 mmol) were then added and the reaction mixture was allowed to stir at 90° C. for 1 h. The reaction mixture was cooled to room temperature and poured into brine (300 ml) then water (50 ml) was added to dissolve the material. This solution was extracted with 9:1 tetrahydrofuran:methyl tert-butyl ether (5×200 ml). The organic extracts were combined washed with brine (2×200 ml), dried over sodium sulfate, and concentrated under reduced pressure to give a dark yellow oil of ethyl 8-fluoro-1-(2-hydroxyethyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate that was carried on to the next reaction without any further purification.

Workup

temperatureThe reaction mixture was cooled to room temperature
dissolutionto dissolve the material
extractionThis solution was extracted with 9:1 tetrahydrofuran
washThe organic extracts were combined washed with brine (2×200 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-37205679ebeb43e598d31cc6c290f32f
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08283361B2

Reaction notes

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