Potassium Hydroxide → 1-Chloro-6-fluoro-2-aminonaphthalene

HRID 1270769Notes

Reaction equation

HRID 1270769 reaction equation
C(OC(=O)[NH:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:16])[CH:12]=2)[C:7]=1[Cl:17])C.[OH-].[K+]>C(O)C>[Cl:17][C:7]1[C:8]2[C:13](=[CH:12][C:11]([F:16])=[CH:10][CH:9]=2)[CH:14]=[CH:15][C:6]=1[NH2:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68805760N-(1-chloro-6-fluoro-2-naphthyl)carbamic acid ethyl ester

Product 1

HCID 184514831-Chloro-6-fluoro-2-aminonaphthalene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(1-chloro-6-fluoro-2-naphthyl)carbamic acid ethyl ester (600 mg, 2.24 mmol) and KOH (1.51 g, 26.9 mmol) in ethanol (20 mL) is heated to reflux temperature under N2 atmosphere for 12 hours. After cooling, the reaction mixture is concentrated by rotary evaporator. The residual oil is purified by flash chromatography on silica gel (3:1 hexanes/EtOAc) to give 1-chloro-6-fluoro-2-aminonaphthalene as a brown solid.

Workup

  1. temperatureis heated
  2. temperatureto reflux temperature under N2 atmosphere for 12 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated by rotary evaporator
  5. customThe residual oil is purified by flash chromatography on silica gel (3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-99f366b8e9874aa299d46b023460aedf
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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