Water → 1-Chloro-7-trifluoromethyl-2-aminonaphthalene

HRID 1270759Notes

Reaction equation

HRID 1270759 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:16]C(=O)C.O.S(=O)(=O)(O)O>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:16]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 18451486HCID 18451486, compound

Product 1

HCID 184514871-Chloro-7-trifluoromethyl-2-aminonaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-7-trifluoromethyl-2-acetamidonaphthalene (700 mg, 2.43 mmol), water (3 mL) and concentrated sulfuric acid (3 mL in ethanol (6 mL) is heated to reflux temperature under a N2 atmosphere for 1 hour. After cooling to room temperature, the mixture is extracted with EtOAc. The extracts are washed with water, brine, dried (Na2SO4) and concentrated. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives 1-chloro-7-trifluoromethyl-2-aminonaphthalene as a white solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature under a N2 atmosphere for 1 hour
  3. extractionthe mixture is extracted with EtOAc
  4. washThe extracts are washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-391daaa983604245b8dadcbb8a961258
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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