Hydrochloric Acid → 4-Chloro-3-fluoro-2-(2-hydroxyethyl)aniline

HRID 1656740Notes

Reaction equation

HRID 1656740 reaction equation
Cl.O.C(O)C.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([CH2:16][CH2:17][OH:18])[C:8]=1[F:19]>[Fe].C(OCC)(=O)C>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([CH2:16][CH2:17][OH:18])[C:8]=1[F:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 20083098HCID 20083098, compound

Product 1

HCID 200831314-Chloro-3-fluoro-2-(2-hydroxyethyl)anilineYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4.8 g of iron powder and 0.45 ml of concentrated hydrochloric acid were added to a mixture solvent of 50 ml of water and 10 ml of ethanol, and the solution was heated at 80°-90° C. 6.69 g (31 mmol) of 4-chloro-3-fluoro-2-(2-hydroxyethyl)nitrobenzene was added to the solution through 10 minutes, and the solution was heated for 1 hour as was. After air-cooling, 100 ml of ethyl acetate was added to the solution, and insoluble matter was filtered. The organic layer was separated and was washed with aqueous 10% sodium hydrogen carbonate solution. After drying over magnesium sulfate, the solvent was removed by distillation to obtain 4.68 g of the subject compound (126) in a 80% yield.

Workup

  1. temperaturethe solution was heated at 80°-90° C
  2. temperaturethe solution was heated for 1 hour
  3. temperatureAfter air-cooling
  4. filtrationwas filtered
  5. customThe organic layer was separated
  6. washwas washed with aqueous 10% sodium hydrogen carbonate solution
  7. dry with materialAfter drying over magnesium sulfate
  8. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-221d3885f8fb4f0aa07dde67a7f36002
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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