Nitric Acid → HCID 67426897, compound

HRID 2235358Notes

Reaction equation

HRID 2235358 reaction equation
[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:14](=[O:16])[CH3:15])[CH:11]=2)[N:6]([CH3:17])[C:5]1=[O:18])([CH3:3])[CH3:2].[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[CH:1]([CH:4]1[C:12]2[C:7](=[CH:8][C:9]([N+:19]([O-:21])=[O:20])=[C:10]([NH:13][C:14](=[O:16])[CH3:15])[CH:11]=2)[N:6]([CH3:17])[C:5]1=[O:18])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 23092679HCID 23092679, compound

Product 1

HCID 67426897HCID 67426897, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
0 °C

Procedure

(rac)-N-(3-Isopropyl-1-methyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide is dissolved in acetic acid (3 ml) and cooled to 0° C. Then nitric acid (fuming, 1.5 ml) is added drop-wise and the reaction mixture is stirred for 30 min at this temperature. After completion of the reaction the mixture is poured into ice-water and extracted with CH2Cl2. The combined organic layer is washed with water, dried over MgSO4 and evaporated. The residue is subjected to flash chromatography on silica gel eluting with light petroleum/EtOAc to give the pure compound (1.7 g).

Workup

  1. customAfter completion of the reaction the mixture
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer is washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-35e12d64395c4cc2987caef824baa35d
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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