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

HRID 1804934Notes

Reaction equation

HRID 1804934 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-ethyl-2,3-dihydro-1H-indole (2.5 g, 17 mmol) in H2SO4 (98%, 20 mL) was slowly added KNO3 (1.7 g, 17 mmol) at 0° C. After addition, the mixture was stirred at 0-10° C. for 10 min, 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 column chromatography on silica gel to give 5-ethyl-6-nitro-2,3-dihydro-1H-indole (1.9 g, 58%).

Workup

  1. customat 0° C
  2. additionAfter addition
  3. additioncarefully poured into ice
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-826495bff68946dba0477903f2e6707d
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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