Nitric Acid → N-Acetyl-7-cyano-5-nitroindoline

HRID 4929Notes

Reaction equation

HRID 4929 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:22]#[N:23])[CH2:15][CH2:14]1)(=[O:12])[CH3:11]>C(O)(=O)C>[C:10]([N:13]1[C:21]2[C:16](=[CH:17][C:18]([N+:6]([O-:9])=[O:7])=[CH:19][C:20]=2[C:22]#[N:23])[CH2:15][CH2:14]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 14361370HCID 14361370, compound

Product 1

HCID 19797206N-Acetyl-7-cyano-5-nitroindolineYield 66.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixed solution of acetic acid (3.8 ml), concentrated sulfuric acid (4.7 ml) and funing nitric acid (0.8 ml), under cooling with stirring, were added only small portions of N-acetyl-7-cyano-indoline (2.42 g). After stirred at the temperature as such for 7.5 hours, the reaction mixture was poured into ice-water (50 ml). The deposited crystal was collected by filtration, washed with water and acetone, and then dried to give the intended compound 2.6 g (66.7%) as white powder. M.P.: 245°-255° C.

Workup

  1. stirringAfter stirred at the temperature as such for 7.5 hours
  2. filtrationThe deposited crystal was collected by filtration
  3. washwashed with water and acetone
  4. customdried

Sources & evidence

ORD record
ord-431b0132d8ae40649c3dfbbbb5dc0995
Source dataset
uspto-grants-1993_09
Patent number
US05242912

Reaction notes

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