2-Aminophenol → HCID 67498799, compound

HRID 74276Notes

Reaction equation

HRID 74276 reaction equation
[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1O.CCN=C=NCCCN(C)C.CS(O)(=O)=O>O.C(Cl)(Cl)Cl>[F:1][C:2]1[C:10]([C:11]([F:14])([F:13])[F:12])=[CH:9][C:5]([C:6]2[O:8][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=2)=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 58012-AminophenolHCID 6395Methanesulfonic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 247210834-Fluoro-3-nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 67498799HCID 67498799, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

4-Fluoro-3-nitro-5-trifluoromethyl benzoic acid (1.00 g, 4.0 mmol), 2-aminophenol (0.47 g, 4.4 mmol), CHCl3 (20 mL), and WSC (0.83 g, 4.4 mmol) were added together and stirred at room temperature for 1 hour. Water was added, and this was extracted with chloroform/acetone (3:1). After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To a dioxane (20 mL) solution of the solid obtained was added methanesulfonic acid (2.28 g, 24 mmol), and this was heated to reflux for 18 hours. After the reaction solution was cooled, water was added, and the precipitated crystals were filtered, and after being washed with water were dried to yield the title compound (0.70 g, 54% yield) as yellowish-brown crystals.

Workup

  1. extractionthis was extracted with chloroform/acetone (3:1)
  2. customAfter the organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate, it
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customTo a dioxane (20 mL) solution of the solid obtained
  7. temperaturethis was heated
  8. temperatureto reflux for 18 hours
  9. temperatureAfter the reaction solution was cooled
  10. filtrationthe precipitated crystals were filtered
  11. washafter being washed with water
  12. customwere dried

Sources & evidence

ORD record
ord-0dc74182660c4a3da132fb85ca1a5fa0
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

Loading…