4-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene → 4-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

HRID 1609062Notes

Reaction equation

HRID 1609062 reaction equation
C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:15][CH2:16][OH:17])[C:7]=1[F:18])(C)(C)C>Cl>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([CH2:15][CH2:16][OH:17])[C:7]=1[F:18]

Participants

3

Reactant 1

HCID 224753164-t-Butylamino-3-fluoro-2-(2-hydroxyethyl)nitrobenzene

Product 1

HCID 207922134-Amino-3-fluoro-2-(2-hydroxyethyl)nitrobenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

11 g of the compound (123) obtained in Comparative Example 5 was added to 200 ml of concentrated hydrochloric acid, and the solution heated at reflux for 2.5 hours. After air-cooling, the solution was extracted with 500 ml of ethyl acetate four times, and the extract was washed with aqueous 10% sodium hydrogen carbonate solution. After drying over magnesium sulfate, the solvent was removed by distillation. The residue was crystallized with n-hexane, and the crystals were filtered to obtain 8.33 g of the subject compound (124) in a 97% yield.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter air-cooling
  4. extractionthe solution was extracted with 500 ml of ethyl acetate four times
  5. washthe extract was washed with aqueous 10% sodium hydrogen carbonate solution
  6. dry with materialAfter drying over magnesium sulfate
  7. customthe solvent was removed by distillation
  8. customThe residue was crystallized with n-hexane
  9. filtrationthe crystals were filtered

Sources & evidence

ORD record
ord-86fabac36be04726945251ec5bb74174
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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