Sodium Hydroxide → 5-ethyl-6-nitro-2,3-dihydro-1H-indole

HRID 468404Notes

Reaction equation

HRID 468404 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH2:6]2)[CH3:2].[N+:12]([O-])([O-:14])=[O:13].[K+].[OH-].[Na+]>OS(O)(=O)=O>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][CH2:7][CH2:6]2)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 167881195-ethyl-2,3-dihydro-1H-indole

Product 1

HCID 574702055-ethyl-6-nitro-2,3-dihydro-1H-indoleYield 58.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 5-ethylindoline (2.5 g, 17 mmol) in H2SO4 (98%, 20 mL) was slowly added KNO3 (1.7 g, 17 mmol) at 0° C. The mixture was stirred at 0-10° C. for 10 minutes. The mixture was then carefully poured into ice, basified with NaOH solution to pH 9, and extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4 and concentrated to dryness. The residue was purified by silica column to give 5-ethyl-6-nitroindoline (1.9 g, 58%).

Workup

  1. customat 0° C
  2. additionThe mixture was then carefully poured into ice
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by silica column

Sources & evidence

ORD record
ord-947e4326cc2344fb9ca585b4b9ae0a26
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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