Nitric Acid → 1-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

HRID 1107961Notes

Reaction equation

HRID 1107961 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[CH:20]=2)[CH:15]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14]1)(=[O:12])[CH3:11]>CC(O)=O>[C:10]([N:13]1[C:21]2[C:16](=[C:17]([CH3:24])[C:18]([Br:23])=[C:19]([CH3:22])[C:20]=2[N+:6]([O-:9])=[O:7])[CH:15]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14]1)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 222473121-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline

Product 1

HCID 222473011-Acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of AcOH (10 ml), conc. sulfuric acid (10 ml) and nitric acid (0.55 ml) was added by portions 1-acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethylindoline (3.0 g) at 0° C., and the mixture was stirred at the same temperature for 5 hr. The reaction mixture was poured into ice water and extracted with CHCl3 (100 ml). After washing with water, the mixture was dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1) to give 2.7 g of 1-acetyl-5-bromo-3-(2-ethoxycarbonylethyl)-4,6-dimethyl-7-nitroindoline.

Workup

  1. extractionextracted with CHCl3 (100 ml)
  2. washAfter washing with water
  3. dry with materialthe mixture was dried over anhydrous sodium sulfate
  4. customCHCl3 was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=50/1-10/1)

Sources & evidence

ORD record
ord-0e082bf8ae26440f8c402de03159277c
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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