Acetic Acid → 6-iodo-3,4-dihydronaphthalen-1(2H)-one

HRID 492091Notes

Reaction equation

HRID 492091 reaction equation
S(O)(O)(=O)=O.N[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2.C(O)(=O)C.N([O-])=O.[Na+].[I-:26].[K+]>O>[I:26][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[C:13](=[O:17])[CH2:12][CH2:11][CH2:10]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4875Potassium IodideHCID 23668193Sodium NitriteHCID 666513926-amino-3,4-dihydro-2H-naphthalen-1-one sulfate

Product 1

HCID 454898006-iodo-3,4-dihydronaphthalen-1(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To 1.92 g (11.9 mmol) 6-amino-3,4-dihydro-2H-naphthalen-1-one sulfate was added 20 mL water and 20 mL glacial acetic acid. The resulting solution was stirred in an ice bath and a solution of 1.72 grams (25 mmoles) sodium nitrite in 15 mL water was added dropwise over 0.5 hour. The reaction mixture was slowly poured into a well stirred solution of 8 grams (48 mmoles) potassium iodide in 80 mL water. The mixture was extracted with diethyl ether, and the organic phase was washed with water, saturated aqueous sodium hydrogen sulfite, and saturated aqueous sodium chloride. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 5% ethyl acetate in hexane. 6-Iodo-3,4-dihydro-2H-naphthalen-1-one was obtained as a white solid, 3.12 grams (94%), m.p. 77-78°.

Workup

  1. additionThe reaction mixture was slowly poured into a well
  2. extractionThe mixture was extracted with diethyl ether
  3. washthe organic phase was washed with water, saturated aqueous sodium hydrogen sulfite, and saturated aqueous sodium chloride
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-05a07e81b4b84190b8671bfb32e2ad39
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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