Potassium Iodide → 8-Iodo-2-naphthol

HRID 2306258Notes

Reaction equation

HRID 2306258 reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.N([O-])=O.[Na+].[I-:17].[K+]>C1COCC1.Cl.O.CCOC(C)=O>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[I:17])=[CH:7][CH:8]=1

Participants

8

Reactant 3

HCID 4875Potassium IodideHCID 83588-Amino-2-naphthalenolHCID 23668193Sodium Nitrite

Product 1

HCID 6229868-Iodo-2-naphthol

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-amino-2-naphthol (10.0 g, 62.80 mmol) in THF (50 mL) and 3 N aqueous HCl (100 mL) at 0° C. was added a solution of NaNO2 (4.76 g, 69.08 mmol) in H2O (20 mL). The resulting mixture was stirred for 15 min, then a solution of potassium iodide (41.8 g, 251.8 mmol) in H2O (30 mL) was added. After 40 min, the reaction was diluted with EtOAc and filtered. The filtrate was extracted with EtOAc (2×), the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo in the presence of silica gel. The powder was chromatographed on silica gel, eluting with hexane—10% EtOAc, to yield the above-titled compound.

Workup

  1. waitAfter 40 min
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with EtOAc (2×)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo in the presence of silica gel
  7. customThe powder was chromatographed on silica gel
  8. washeluting with hexane—10% EtOAc

Sources & evidence

ORD record
ord-b163e0ce6af941f28bf533a138489b6f
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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