Nitric Acid → HCID 10587804, compound

HRID 2258561Notes

Reaction equation

HRID 2258561 reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[C:9]([Cl:12])[C:8]([OH:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:14]([O-])([OH:16])=[O:15]>C[N+]([O-])=O>[Cl:12][C:9]1[C:10]([CH3:11])=[C:2]([Cl:1])[C:3]([C:4]([OH:6])=[O:5])=[C:7]([N+:14]([O-:16])=[O:15])[C:8]=1[OH:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 10680480HCID 10680480, compound

Product 1

HCID 10587804HCID 10587804, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

2,4-Dichloro-5-hydroxy-3-methylbenzoic acid (90 mg, 0.41 mmol) was mixed with CH3NO2 (9 mL) and heated to 40 --C. To the solution was added HNO3 (20 μL, 90%, 0.43 mmol) and the reaction mixture was stirred at room temperature for 4 h. Evaporation of the solvent followed by vacuum-drying over KOH gave 112 mg of a crude product. Purification by flash column chromatography (SiO2, EtOAc-HOAc 30:1) afforded 79 mg of the title compound. Mp: 199° C. (dec); 1H NMR (DMSO-d6): δ 2.45 (s, 3H); 13C NMR (DMSO-d6): δ 164.27, 147.05, 139.61, 136.27, 128.35, 126.46, 118.87, 18.62; MS (EI, 70 eV): m/z (rel.int.) 267/265 (M+, 66/100), 249/248 (67/85), 205/203 (28/54).

Workup

  1. temperatureheated to 40
  2. customEvaporation of the solvent
  3. dry with materialby vacuum-drying over KOH
  4. customgave 112 mg of a crude product
  5. customPurification by flash column chromatography (SiO2, EtOAc-HOAc 30:1)

Sources & evidence

ORD record
ord-b609922e0a8e4eee9e5b19e7f5c93851
Source dataset
uspto-grants-1997_08
Patent number
US05661183

Reaction notes

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