Sodium Bicarbonate → 1-Fluoronaphthalen-2-amine

HRID 1270749Notes

Reaction equation

HRID 1270749 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:12]C(=O)C.C([O-])(O)=O.[Na+]>Cl.CCO>[F:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 13663774HCID 13663774, compound

Product 1

HCID 222867781-Fluoronaphthalen-2-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1.31 g (6.43 mmol) of 1-fluoro-2-acetylaminonaphthalene in 15 mL of 6 N HCl and 15 mL of EtOH under a nitrogen atmosphere is heated to reflux for 3 hours and then allowed to cool to room temperature. The reaction is neutralized with saturated aqueous NaHCO3 and extracted 3 times with 30 mL of CH2Cl2. The combined organic layers are washed 2 times with 20 mL saturated brine, dried over MgSO4 and the solvents evaporated to give 1-fluoro-2-aminonaphthalene.

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 hours
  3. extractionextracted 3 times with 30 mL of CH2Cl2
  4. washThe combined organic layers are washed 2 times with 20 mL saturated brine
  5. dry with materialdried over MgSO4
  6. customthe solvents evaporated

Sources & evidence

ORD record
ord-c3e35ad4c0074288ad013208ee4af736
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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