Hydrochloric Acid → HCID 13277116, compound

HRID 1532191Notes

Reaction equation

HRID 1532191 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:16]([O-])=O)[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Sn].Cl.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:16])[CH:5]=[C:6]([Cl:15])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5352426Tin atomHCID 22728118HCID 22728118, compound

Product 1

HCID 13277116HCID 13277116, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 3,5-dichloro-4-phenoxy-nitrobenzene (6.1 g) and tin powder (12 g) is added dropwise concentrated hydrochloric acid (60 mL). Ethanol (60 mL) is added and the mixture is heated to reflux for approximately 1 hour. The mixture is then cooled in an ice bath and basified by addition of solid sodium hydroxide. The resulting suspension is filtered through a pad of diatomaceous earth and extracted three times with ethyl acetate. The combined organic extracts are then washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide the desired product as a yellow solid. Recrystallization from ethyl acetate-hexanes provided the product as a pale yellow solid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for approximately 1 hour
  3. temperatureThe mixture is then cooled in an ice bath
  4. filtrationThe resulting suspension is filtered through a pad of diatomaceous earth
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic extracts are then washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-57b527d88c6249329321c65e9c92497a
Source dataset
uspto-grants-2001_03
Patent number
US06201013B1

Reaction notes

Loading…