Water → N-(6-Nitro-1-oxo-indan-5-yl)-acetamide

HRID 2196858Notes

Reaction equation

HRID 2196858 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][C:5]=1[NH:13][C:14](=[O:16])[CH3:15])([O-:3])=[O:2].[OH2:17]>CC(O)=O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=[O:17])=[CH:6][C:5]=1[NH:13][C:14](=[O:16])[CH3:15])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962Water2×HCID 10751392N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 15084115N-(6-Nitro-1-oxo-indan-5-yl)-acetamideYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
17.5 °C

Procedure

A solution of CrO3 (26.5 g) in a mixture of 15 ml of H2O and 235 ml of AcOH was prepared by sonicating the suspension for 45 min. The resulting solution was added dropwise to a cooled solution of N-(6-nitro-indan-5-yl)-acetamide (22 g, 0.1 mol) in Ac20 (2.5 L) while maintaining the temperature between 15-20° C. After the addition was completed, the mixture was stirred at 25° C. overnight, poured into 10 L of water, and stirred for 1 h. The solution was then extracted with two 2-L portions of CH2Cl2. The organic layers were combined, and concentrated to 500 ml, washed with two 50-ml portions of 10% NaOH followed by water, and then dried (Na2SO4). The solvent was removed, leaving a yellow powder (16 g, 75%), which was used for next step without further purification.

Workup

  1. customwas prepared
  2. customby sonicating the suspension for 45 min
  3. additionAfter the addition
  4. stirringstirred for 1 h
  5. extractionThe solution was then extracted with two 2-L portions of CH2Cl2
  6. concentrationconcentrated to 500 ml
  7. washwashed with two 50-ml portions of 10% NaOH
  8. dry with materialdried (Na2SO4)
  9. customThe solvent was removed

Sources & evidence

ORD record
ord-1e9fc781adc74b56b4c3dcacbded3877
Source dataset
uspto-grants-2012_12
Patent number
US08338487B2

Reaction notes

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