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

HRID 1781048Notes

Reaction equation

HRID 1781048 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2].[N+:14]([O-])([O-:16])=[O:15].[K+]>OS(O)(=O)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[CH2:10][CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamideYield 15.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5.59 g (31.9 mmol) of 5-acetamidoindan in 55 mL of H2SO4 kept in an ice-bath was added portionwise 3.62 g of KNO3 (35.8 mmol). The solution was stirred in the ice-bath for 2 h and at room temperature overnight. It was added to 500 mL of ice-water and stirred for 1 h. The precipitate was filtered, washed with water, and dried to leave a black solid, which was separated by chromatography (silica gel, eluted with hexane/ethyl acetate=10:1) to give 1.06 g (15%) of a yellow solid. 1H NMR (CDCl3), 2.142 (m, 2), 2.279 (s, 3), 3.00 (m, 4), 8.44 (s, 1), 8.575 (s, 1), 10.389 (s, 1).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customto leave a black solid, which
  5. customwas separated by chromatography (silica gel, eluted with hexane/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-6422effaf4d74f519eb3d457fcdf3521
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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