Nitric Acid → HCID 69068910, compound

HRID 2374484Notes

Reaction equation

HRID 2374484 reaction equation
[CH2:1]([C:3]1([CH2:20][CH3:21])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]1=[O:19])[CH3:2].[N+:22]([O-:25])([OH:24])=[O:23]>S(=O)(=O)(O)O>[CH2:20]([C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[CH:7][C:8]([N+:22]([O-:24])=[O:23])=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]([CH:16]([CH3:17])[CH3:18])[C:4]1=[O:19])[CH3:21].[CH2:20]([C:3]1([CH2:1][CH3:2])[C:11]2[C:6](=[C:7]([N+:22]([O-:25])=[O:23])[CH:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[CH:10]=2)[N:5]([CH:16]([CH3:17])[CH3:18])[C:4]1=[O:19])[CH3:21]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 69073814HCID 69073814, compound

Product 2

HCID 69067380HCID 69067380, compoundHCID 69068910HCID 69068910, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of N-(3,3-diethyl-1-isopropyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (10.4 g, 36.06 mmol) in conc. sulfuric acid (50 ml) was added slowly a mixture of nitric acid (65%, 3.84 g, 2.72 ml, 39.67 mmol) and conc. sulfuric acid (10 ml) at 0° C. After 2 h at room temperature the mixture was poured into ice water. The precipitate was filtered off, washed with water and dried. The crude material was purified by silica gel chromatography (isohexane/ethyl acetate 1:1) to yield 2.2 g N-(3,3-diethyl-1-isopropyl-6-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (6.60 mmol, 18%) besides undesired N-(3,3-diethyl-1-isopropyl-7-nitro-2-oxo-2,3-dihydro-1H-indol-5-yl)-acetamide (5.5 g).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried
  4. customThe crude material was purified by silica gel chromatography (isohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-f1e2616bd1f9410e885ccf05f3ffb9b5
Source dataset
uspto-grants-2008_12
Patent number
US07462639B2

Reaction notes

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