Sodium Nitrate → 7-Nitro-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 1613609Notes

Reaction equation

HRID 1613609 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[CH2:4][CH2:3][CH2:2]1.[N+:13]([O-])([O-:15])=[O:14].[Na+]>S(=O)(=O)(O)O>[N+:13]([C:10]1[CH:9]=[CH:8][C:7]2[O:1][CH2:2][CH2:3][CH2:4][C:5](=[O:12])[C:6]=2[CH:11]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24268Sodium Nitrate2×HCID 3155752,3,4,5-Tetrahydro-1-benzoxepin-5-one

Product 1

HCID 145805137-Nitro-3,4-dihydro-1-benzoxepin-5(2H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

40.5 g (0.25 mole) of 2,3-dihydro-1-benzoxepin-5(4H)-one are introduced at -10° C. into 400 ml of concentrated sulfuric acid while stirring. Coarsely crystalline sodium nitrate is slowly introduced at -5° C. to 0° C. whilst stirring vigorously. The mixture is then stirred at 0° C. for about 1 hour, during which the sodium nitrate slowly dissolves. The mixture is stirred into ice/water and, after about 30 minutes, filtered with suction and washed thoroughly with water. The residue on the filter is taken up in ethyl acetate, and the solution is separated from the water, dried over sodium sulfate, filtered and evaporated in vacuo. The residue is crystallized in ethyl acetate/cyclohexane.

Workup

  1. stirringwhilst stirring vigorously
  2. dissolutionslowly dissolves
  3. filtrationfiltered with suction
  4. washwashed thoroughly with water
  5. customthe solution is separated from the water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe residue is crystallized in ethyl acetate/cyclohexane

Sources & evidence

ORD record
ord-6bc8040910794cf2bb3a55f1f8da6d15
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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