Toluene → 1-Methyl-6-nitroindoline

HRID 1939166Notes

Reaction equation

HRID 1939166 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1(C)C=CC=CC=1.[N+:18]([C:21]1[CH:29]=[C:28]2[C:24]([CH2:25][CH2:26][NH:27]2)=[CH:23][CH:22]=1)([O-:20])=[O:19].IC>O1CCCC1.CO>[CH3:11][N:27]1[C:28]2[C:24](=[CH:23][CH:22]=[C:21]([N+:18]([O-:20])=[O:19])[CH:29]=2)[CH2:25][CH2:26]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 297576-NitroindolineHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 123690471-Methyl-6-nitroindoline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Potassium bis(trimethylsilyl)amide (67 ml of a 0.5M toluene solution) was added slowly to a stirred solution of 6-nitroindoline (5.0 g) in anhydrous tetrahydrofuran (200 ml) at -78° C. under a nitrogen atmosphere. Iodomethane (2.09 ml) was added then the reaction mixture was allowed to warm to room temperature then stirred overnight. Methanol (5 ml) was added then the solution was evaporated to dryness. The residue was dissolved in diethyl ether (300 ml), washed with water, saturated brine then dried (magnesium sulphate) and evaporated to dryness. The crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)→30% ethyl acetate/petroleum ether (60-80) and the product crystallised from diethyl ether/petroleum ether (60-80) to afford 0.9 g.

Workup

  1. customthe solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in diethyl ether (300 ml)
  3. washwashed with water, saturated brine
  4. dry with materialthen dried (magnesium sulphate)
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography on silica using 10% ethyl acetate/petroleum ether (60-80)→30% ethyl acetate/petroleum ether (60-80)
  7. customthe product crystallised from diethyl ether/petroleum ether (60-80)
  8. customto afford 0.9 g

Sources & evidence

ORD record
ord-7050f3be52e54fcc98c5f41695d63839
Source dataset
uspto-grants-1997_12
Patent number
US05696110

Reaction notes

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