Nitric Acid → HCID 53918291, compound

HRID 259931Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([CH2:11][CH2:12][CH3:13])[C:8]([OH:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:15]([O-])([OH:17])=[O:16]>[N+](C)([O-])=O>[F:1][C:2]1[C:3]([C:4]([OH:6])=[O:5])=[C:7]([N+:15]([O-:17])=[O:16])[C:8]([OH:14])=[C:9]([CH2:11][CH2:12][CH3:13])[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2-Fluoro-5-hydroxy-4-propylbenzoic acid (500 mg, 2.52 mmol) was dissolved in nitromethane (50 mL) through heating to 40° C. and nitric acid (90%, 120 μL, 2.52 mmol) was added. After 10 min at 40° C. followed by reaction at room temperature for 2 h the solvent was evaporated. The residue was dissolved in EtOAc (150 mL), washed with brine (10 mL), dried (MgSO4) and concentrated to dryness giving 640 mg of crude product. Subsequent purification by flash chromatography (SiO2, EtOAc-HOAc 50:1) afforded pure 6-fluoro-3-hydroxy-2-nitro-4-propylbenzoic acid (294 mg). Mp: 128.0°-129.0° C. 1H NMR (DMSO-d6); δ10.2 (br, 1H), 7.39 (d, J=10.4 Hz, 1H), 2.63 (t, J=7.6 Hz, 2H), 1.55 (m, J=7.5 HZ, 2H), 0.89 (t, J=7.4 Hz, 3H). 13C NMR (DMSO-d6): δ162.49, 151.66 (d, J=245 Hz), 143.69, 138.74 (d, J=5 Hz), 138.17 (d, J=8 Hz), 120.25 (d, J=23 Hz), 113.82 (d, J=21 Hz), 31.44, 21.92, 13.60. MS (EI, 70 eV): m/z (rel. int) 243 (M+, 88).

Workup

customAfter 10 min at 40° C. followed by reaction at room temperature for 2 h the solvent
customwas evaporated
dissolutionThe residue was dissolved in EtOAc (150 mL)
washwashed with brine (10 mL)
dry with materialdried (MgSO4)
concentrationconcentrated to dryness
customgiving 640 mg of crude product
customSubsequent purification by flash chromatography (SiO2, EtOAc-HOAc 50:1)

Sources & evidence

ORD record: ord-7820f9fbe27e463ead0aaa77fe27647a
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05523475

Reaction notes

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