Nitric Acid → HCID 53918291, compound

HRID 1418535Notes

Reaction equation

HRID 1418535 reaction equation
FC1C=C(CCC)C(O)=CC=1C(O)=O.[F:15][C:16]1[C:21]([C:22]([OH:24])=[O:23])=[C:20]([N+:25]([O-:27])=[O:26])[C:19]([OH:28])=[C:18]([CH2:29][CH2:30][CH3:31])[CH:17]=1.[N+]([O-])(O)=O>[N+](C)([O-])=O>[F:15][C:16]1[C:21]([C:22]([OH:24])=[O:23])=[C:20]([N+:25]([O-:27])=[O:26])[C:19]([OH:28])=[C:18]([CH2:29][CH2:30][CH3:31])[CH:17]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 86753893HCID 86753893, compound

Product 1

HCID 53918291HCID 53918291, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
40 °C

Procedure

6-Fluoro-3-hydroxy-2-nitro-4-propylbenzoic acid 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); δ 10.2 (br, 1 H), 7.39 (d, J=10.4 Hz, 1 H), 2.63 (t, J=7.6 Hz, 2 H), 1.55 (m, J=7.5 HZ, 2 H), 0.89 (t, J=7.4 Hz, 3 H). 13C NMR (DMSO-d6): δ 162.49, 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

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

Sources & evidence

ORD record
ord-72c67ba7943b48ea92dbe9e63f99e353
Source dataset
uspto-grants-1999_03
Patent number
US05883129

Reaction notes

Loading…