Nitric Acid → HCID 14835236, compound

HRID 1761869Notes

Reaction equation

HRID 1761869 reaction equation
[CH:1]([NH:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)=[O:2].[N+:13]([O-])([OH:15])=[O:14]>>[CH:1]([NH:3][CH:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:13]([O-:15])=[O:14])[CH:10]=2)[CH2:5]1)=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 14835235N-(2,3-Dihydro-1H-inden-2-yl)formamide

Product 1

HCID 14835236HCID 14835236, compound

Procedure

2-Formylaminoindane (15 g) was added portionwise to fuming nitric acid (30 ml, density=1.5 g/ml) whilst keeping the temperature at between 0° and -5°. Stirring was continued for 1 hour at 0° before pouring the reaction mixture onto ice/water and extracting with methylene chloride. The organic layer was washed with aqueous sodium bicarbonate, dried (MgSO4) and evaporated in vacuo to give an oil which was purified by column chromatography on silica eluting with methylene chloride containing hexane (20% down to 0%) and then methylene chloride containing methanol (0% up to 2%). The product-containing fractions were combined and evaporated to give the title compound, yield 7.7 g, m.p. 91°-92°.

Workup

  1. customat between 0° and -5°
  2. additionbefore pouring the reaction mixture onto ice/water
  3. extractionextracting with methylene chloride
  4. washThe organic layer was washed with aqueous sodium bicarbonate
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customto give an oil which
  8. customwas purified by column chromatography on silica eluting with methylene chloride
  9. additioncontaining hexane (20% down to 0%)
  10. additionmethylene chloride containing methanol (0% up to 2%)
  11. customevaporated

Sources & evidence

ORD record
ord-d8c42301746f4f1592e224c2da08dc75
Source dataset
uspto-grants-1989_05
Patent number
US04829071

Reaction notes

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