Nitric Acid → 2-Cyano-5-nitroindane

HRID 1708558Notes

Reaction equation

HRID 1708558 reaction equation
[N+:1]([O-:4])(O)=[O:2].[C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)#[N:6]>C(OC(=O)C)(=O)C>[C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:1]([O-:4])=[O:2])[CH:13]=2)[CH2:8]1)#[N:6]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 232396182,3-Dihydro-1H-indene-2-carbonitrile

Product 1

HCID 189589622-Cyano-5-nitroindaneYield 81%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Fuming nitric acid (40 ml, 1.5 g/ml) was added dropwise with stirring to acetic anhydride (80 ml ) keeping the temperature of the mixture at 0° C. After the addition was complete 2-cyanoindane (11.33 g, 79.5 mmol), (J. Chem. Soc. (B), (1969), 1197) was added dropwise with stirring over 30 minutes maintaining the reaction temperature between -5° and 0° C. The mixture was stirred for a further 15 minutes then poured onto ice. The mixture was extracted with dichloromethane (4×150 ml) and the extracts were washed with saturated aqueous sodium bicarbonate (3×150 ml), dried over magnesium sulphate and the solvent evaporated under reduced pressure. The residue was recrystallised from ethanol to give 2-cyano-5-nitroindane (12.09 g, 81%) as a yellow solid, m.p. 80°-82° C.

Workup

  1. customat 0° C
  2. additionAfter the addition
  3. additionwas added dropwise
  4. temperaturemaintaining the reaction temperature between -5° and 0° C
  5. stirringThe mixture was stirred for a further 15 minutes
  6. additionthen poured onto ice
  7. extractionThe mixture was extracted with dichloromethane (4×150 ml)
  8. washthe extracts were washed with saturated aqueous sodium bicarbonate (3×150 ml)
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent evaporated under reduced pressure
  11. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-d98ba50076f94851a87b012e7c1c7191
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

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