Hydrochloric Acid → HCID 22663538, compound

HRID 392388Notes

Reaction equation

HRID 392388 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=1[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C.[Fe]>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][CH:22]=[CH:21][C:10]=1[O:11][C:12]1[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22663619HCID 22663619, compound

Product 1

HCID 22663538HCID 22663538, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

4-(2-Benzyloxyphenoxy)nitrobenzene (2.57 g, 8 mmol) was dissolved in reagent grade ethanol (20 mL) and treated with concentrated aqueous hydrochloric acid (2.5 mL). The solution was heated to 55° C. under nitrogen, then cautiously treated with iron powder (3.1 g, 55 mmol) in portions with cooling needed after initial exotherm to 75° C. After addition was complete, stirring was continued at 50-60° C. for 45 minutes, then the mixture was cooled to room temperature and filtered through celite® (rinse filter cake with dichloromethane). The filtrate was concentrated in vacuo, the residue dissolved in dichloromethane and the solution washed with saturated aqueous sodium carbonate. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic solution was dried (sodium sulfate), concentrated in vacuo, and chromatographed on silica gel (eluted with dichloromethane, then 10% ethyl acetate/dichloromethane, then 20% ethyl acetate/dichloromethane) to afford the title compound (2.22 g, 95%) as a tan solid; mp 111-112.5° C. 1H NMR: 7.30 (m,4H), 7.20-7.30 (m,1H), 6.97 (m,2H), 6.80-6.90 (m,4H), 6.60-6.65 (m,2H), 5.12 (s,2H), 3.50 (br s, 2H).

Workup

  1. temperaturewith cooling
  2. customto 75° C
  3. additionAfter addition
  4. temperaturethe mixture was cooled to room temperature
  5. filtrationfiltered through celite® (rinse filter cake with dichloromethane)
  6. concentrationThe filtrate was concentrated in vacuo
  7. dissolutionthe residue dissolved in dichloromethane
  8. washthe solution washed with saturated aqueous sodium carbonate
  9. customThe organic layer was separated
  10. extractionthe aqueous layer extracted with dichloromethane
  11. dry with materialThe combined organic solution was dried (sodium sulfate)
  12. concentrationconcentrated in vacuo
  13. customchromatographed on silica gel (
  14. washeluted with dichloromethane

Sources & evidence

ORD record
ord-1005f5c91bd74f39be2d15bb94f8c20f
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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