Nitric Acid → N-(5-Nitro-indan-2-ylmethyl)-propionamide

HRID 450729Notes

Reaction equation

HRID 450729 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[CH2:10][NH:11][C:12](=[O:15])[CH2:13][CH3:14].OS(O)(=O)=O.[N+:21]([O-])([OH:23])=[O:22].O>[N+](C)([O-])=O>[N+:21]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[CH2:1][CH:2]([CH2:10][NH:11][C:12](=[O:15])[CH2:13][CH3:14])[CH2:3]2)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 67023907N-Indan-2-ylmethyl-propionamide

Product 1

HCID 67023929N-(5-Nitro-indan-2-ylmethyl)-propionamideYield 96%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Conditions

Temperature
5 °C

Procedure

N-Indan-2-ylmethyl-propionamide (4.00 g, 19.7 mmol) was dissolved in nitromethane (60 mL) and added to a mixture of concentrated H2SO4 (19 mL), concentrated nitric acid (1.4 mL) and water (3.2 mL) cooled to 5° C. After stirring for 45 min, the reaction solution was poured into water, extracted with ethyl acetate and the organic phase separated and dried over MgSO4. The filtered solution was concentrated to give a brown oil (4.67 g, 96%).

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase separated
  3. dry with materialdried over MgSO4
  4. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-0cfee2d008794240aa8ee69502462c7c
Source dataset
uspto-grants-2013_07
Patent number
US08486984B2

Reaction notes

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