Sodium Carbonate → 2-(tert-Butyl)-6-nitroindoline

HRID 1529618Notes

Reaction equation

HRID 1529618 reaction equation
[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:3])[CH3:2].C(C1NC2C(C=1)=CC=CC=2)(C)(C)C.[N+:27]([O-])([O-:29])=[O:28].[K+].C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[C:1]([CH:5]1[CH2:13][C:12]2[C:7](=[CH:8][C:9]([N+:27]([O-:29])=[O:28])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 5941662-tert-Butyl-1H-indoleHCID 46426432-(tert-Butyl)indoline

Product 1

HCID 574701952-(tert-Butyl)-6-nitroindolineYield 32%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of the mixture of 2-tert-butyl-2,3-dihydro-1H-indole and 2-tert-butyl-1H-indole (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 55.7 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h, carefully poured into cracked ice, basified with Na2CO3 to pH-8 and extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was purified by column chromatography to give 2-tert-butyl-6-nitro-2,3-dihydro-1H-indole (4.0 g, 32% over 2 steps).

Workup

  1. customat 0° C
  2. additioncarefully poured into cracked ice
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c3efb4f733c046e5a4f5a5f9796cca1e
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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