Methanol → 2-fluoro-N1-(3-(tetrahydrofuran-2-yl)propyl)benzene-1,4-diamine

HRID 56219Notes

Reaction equation

[F:1][C:2]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][O:9]1.CO.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[F:1][C:2]1[CH:16]=[C:15]([NH2:17])[CH:14]=[CH:13][C:3]=1[NH:4][CH2:5][CH2:6][CH2:7][CH:8]1[CH2:12][CH2:11][CH2:10][O:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-fluoro-4-nitro-N-(3-(tetrahydrofuran-2-yl)propyl)aniline (480 mg, 1.79 mmol), MeOH (40 mL), water (20 mL), iron powder (504 mg, 9.03 mmol) and NH4Cl (193 mg, 3.61 mmol) was stirred at 60° C. overnight. The mixture was then cooled to rt and saturated NaHCO3 aqueous solution was added. The resulting mixture was filtered and the filtrate was extracted with DCM (30 mL×4). The combined organic layers were washed with brine (40 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as red liquid (260 mg, 61%).

Workup

temperatureThe mixture was then cooled to rt
filtrationThe resulting mixture was filtered
extractionthe filtrate was extracted with DCM (30 mL×4)
washThe combined organic layers were washed with brine (40 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record: ord-53639d55a8134301bc16f923e99fba65
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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