Sodium Hydroxide → 1-Amino-5-fluoronaphthalene

HRID 2110407Notes

Reaction equation

HRID 2110407 reaction equation
[F:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CCO.[Fe]>[NH2:12][C:7]1[C:6]2[C:11](=[C:2]([F:1])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 217302841-Fluoro-5-nitronaphthalene

Product 1

HCID 217302891-Amino-5-fluoronaphthaleneYield 81.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 208A (62 mg, 0.32 mmol) in 1 mL EtOH containing 0.1 mL 12 N HCl was heated to reflux. Iron powder (62 mg, 1.11 mmol) was added in small portions and heating was continued for 2 h. The mixture was cooled, neutralized with 1 N NaOH solution and the aqueous layer was extracted with CH2Cl2. The combined organic phases were dried over MgSO4 and concentrated in vacuo to leave a residue which was purified by flash chromatography on silica gel eluting with 40 to 80% EtOAc in hexanes to give 42 mg (0.26 mmol, 80%) of compound 208B as a yellow solid.

Workup

  1. temperatureheating
  2. temperatureThe mixture was cooled
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto leave a residue which
  7. customwas purified by flash chromatography on silica gel eluting with 40 to 80% EtOAc in hexanes

Sources & evidence

ORD record
ord-60ea18dde7f1487e8ba56bb79d1d3445
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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