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

HRID 1847792Notes

Reaction equation

HRID 1847792 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-89c9a5bb25ce44fa82234ea5c3cdc18c
Source dataset
uspto-grants-2015_02
Patent number
US08952049B2

Reaction notes

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