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

HRID 1836282Notes

Reaction equation

HRID 1836282 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.[C:11]([O:14]C(=O)C)(=O)[CH3:12].[N+:18]([O-])([OH:20])=[O:19]>>[C:11]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:18]([O-:20])=[O:19])[CH2:7][CH2:6][CH2:5]2)(=[O:14])[CH3:12]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 90496Indan-5-amine

Product 1

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

Procedure

5-Amino-indan (3.00 g, 22.53 mmol) was added slowly to acetic anhydride (10 mL) cooled by an ice water bath. After 15 min., 70% HNO3 (3 mL, 46.99 mmol) was carefully added dropwise so that the temperature remained below 26° C. The mixture was allowed to slowly warm to room temperature and stirred for 2 days. It was then treated with ice water (60 mL) and extracted with EtOAc (3×20 mL). The extract was washed with water, Na2CO3 solution, dried (MgSO4), filtered and concentrated to give a dark oil (3.51 g). It was dissolved in CHCl3 and flash chromatographed over silica gel (180 g) eluting with EtOAc/hexane (1:10) to afford a yellowish orange solid (1.43 g, 29% yield): mp 100-104° C.

Workup

  1. temperaturecooled by an ice water bath
  2. customremained below 26° C
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe extract was washed with water, Na2CO3 solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d9d4ce6238c244e5b913626bc41ef217
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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