Hydrochloric Acid → HCID 25156888, compound

HRID 1019743Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1F.[C:14]([O:21][CH3:22])(=[O:20])[CH2:15][C:16]([O:18][CH3:19])=[O:17].[OH-].[Na+].Cl>O.CN1CCCC1=O>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:15]([C:14]([O:21][CH3:22])=[O:20])[C:16]([O:18][CH3:19])=[O:17]

Participants

Conditions

Temperature: 80 °C

Procedure

1-chloro-2-fluoro-4-methoxy-5-nitrobenzene (3.05 g, 14.83 mmol) and dimethyl malonate (2.5 g, 18.84 mmol) were added to N-methylpyrrolidinone (50 mL) at room temperature. Sodium hydroxide (1.25 g, 31.14 mmol) was added and the temperature was raised to 80° C. and maintained for 2 hours. The reaction mass was cooled to 5° C. then 1 N HCl solution was added to adjust the pH to 2. Water (300 mL) was added and the mixture stirred for 15 minute at 5° C. The precipitate was collected by filtration, washed with water (2×10 mL), dissolved in DCM (60 mL), dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 10-20% EtOAc in hexane to give the title compound (3.2 g, 68%) as a solid.

Workup

temperaturemaintained for 2 hours
temperatureThe reaction mass was cooled to 5° C.
filtrationThe precipitate was collected by filtration
washwashed with water (2×10 mL)
dissolutiondissolved in DCM (60 mL)
dry with materialdried (Na2SO4)
customthe solvent removed under reduced pressure
customThe residue was purified by column chromatography on neutral silica gel using 10-20% EtOAc in hexane

Sources & evidence

ORD record: ord-6a7c598bb6644d5d82ac4179f2c80736
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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