Potassium Iodide → 6-iodo-3,4-dihydronaphthalen-1(2H)-one

HRID 971294Notes

Reaction equation

HRID 971294 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6](NC(=O)C)[CH:5]=[CH:4][C:3]1=2.S(O)(O)(=O)=O.NC1C=C2C(=CC=1)C(=O)CCC2.N([O-])=O.[Na+].[I-:37].[K+]>S(=O)(=O)(O)O.O>[I:37][C:6]1[CH:7]=[C:8]2[C:3](=[CH:4][CH:5]=1)[C:2](=[O:1])[CH2:11][CH2:10][CH2:9]2

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 2780190N-(5-Oxo-5,6,7,8-tetrahydronaphthalen-2-yl)acetamideHCID 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 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)-acetamide 2.5 grams (12.3 mmole) in 20 mL 20% sulfuric acid was heated at 90° for 45 minutes. The solution was allowed to cool to room temperature whereupon 6-amino-3,4-dihydro-2H-naphthalen-1-one sulfate (not shown) precipitated as a solid mass. To this solid 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 200 mL ethyl ether, and the organic phase was washed with water, then saturated sodium hydrogen sulfite, then with saturated 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. temperaturewas heated at 90° for 45 minutes
  2. customprecipitated as a solid mass
  3. additionTo this solid was added 20 mL water and 20 mL glacial acetic acid
  4. additionThe reaction mixture was slowly poured into a well
  5. extractionThe mixture was extracted with 200 mL ethyl ether
  6. washthe organic phase was washed with water
  7. dry with materialThe organic phase was dried (magnesium sulfate)
  8. concentrationconcentrated under reduced pressure
  9. washeluting with 5% ethyl acetate in hexane

Sources & evidence

ORD record
ord-80dfdb1ac88c44be94455a365cb93944
Source dataset
uspto-grants-2007_12
Patent number
US07312359B2

Reaction notes

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