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

HRID 1403965Notes

Reaction equation

HRID 1403965 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].[N+:14]([O-])([O-:16])=[O:15].[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+:14]([O-:16])=[O:15])=[CH:10][CH:11]=2)[NH:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24434Potassium NitrateHCID 46426432-(tert-Butyl)indoline

Product 1

HCID 574701952-(tert-Butyl)-6-nitroindolineYield 32.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-tert-butylindoline (9.7 g) in H2SO4 (98%, 80 mL) was slowly added KNO3 (5.6 g, 56 mmol) at 0° C. After addition, the reaction mixture was stirred at room temperature for 1 h. The mixture was 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-nitroindoline (4.0 g, 31% over two steps). 1H NMR (300 MHz, CDCl3) δ 7.52 (dd, J=1.8, 8.1 Hz, 1H), 7.30 (s, 1H), 7.08 (d, J=7.8 Hz, 1H), 3.76 (t, J=9.6 Hz, 1H), 2.98-3.07 (m, 1H), 2.82-2.91 (m, 1H), 0.91 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-f3c8f6713671470eb09a8b0b81ec8a85
Source dataset
uspto-grants-2014_12
Patent number
US08912199B2

Reaction notes

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