Nitric Acid → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

HRID 2196857Notes

Reaction equation

HRID 2196857 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[N+:11]([O-:14])(O)=[O:12].[C:15](OC(=O)C)(=[O:17])[CH3:16]>>[N+:11]([C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][CH2:7]2)=[CH:3][C:2]=1[NH:1][C:15](=[O:17])[CH3:16])([O-:14])=[O:12]

Participants

4

Reactant 3

HCID 944Nitric Acid2×HCID 7918Acetic Anhydride3×HCID 90496Indan-5-amine

Product 1

HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamideYield 95%

Procedure

A mixture of 5-aminoindane (13.3 g, 0.1 mol) in 150 ml of acetic anhydride was stirred at room temperature for 3 hours. The reaction mixture was cooled to 0° C., and an ice-cooled solution of 90% nitric acid (d1.4) (8.4 g, 0.12 mol) in 15 ml of acetic anhydride (HNO3 was added dropwise to acetic anhydride with stirring at 0° C.) was added dropwise. After addition, the reaction mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The reaction mixture was poured into 800 ml of ice-water with strong stirring. The precipitate was filtered and washed thoroughly with water and dried at 40° C. to give a yellow solid (20.9 g, 95%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. stirringwith stirring at 0° C.)
  3. additionwas added dropwise
  4. additionAfter addition
  5. stirringthe reaction mixture was stirred at 0° C. for 1 hour
  6. customat room temperature
  7. customovernight
  8. filtrationThe precipitate was filtered
  9. washwashed thoroughly with water
  10. customdried at 40° C.

Sources & evidence

ORD record
ord-b51e1d7475134eda8e4a725a17e38a87
Source dataset
uspto-grants-2012_12
Patent number
US08338487B2

Reaction notes

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