Sodium Carbonate → HCID 18788040, compound

HRID 1106396Notes

Reaction equation

HRID 1106396 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:19](=O)([O-])[O-:20].[Na+].[Na+]>CN(C)C=O>[CH3:1][C:2]1([CH3:18])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:19]=[O:20])[CH:8]=2)[N:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 18788046HCID 18788046, compound

Product 1

HCID 18788040HCID 18788040, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2,2-dimethyl-N-n-heptylindoline (12.5 g) in dimethylformamide (100 cm3) phosphorus oxychloride (15.3 g) was added at 5° C. before heating the mixture at 80° C. for 2-5 hours. The reaction mixture was cooled, poured onto ice, neutralised with solid sodium carbonate and extracted into toluene. The toluene was washed with water, separated, dried over magnesium sulphate, filtered and evaporated to leave an oil. The oil was eluted from silica using dichloromethane as eluent, evaporation of the solvent gave 2,2-dimethyl-5-formyl-N-n-heptylindoline (4.9 g, 36.1%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto ice
  3. extractionextracted into toluene
  4. washThe toluene was washed with water
  5. customseparated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customto leave an oil
  10. washThe oil was eluted from silica
  11. customevaporation of the solvent

Sources & evidence

ORD record
ord-b802d7fb2beb44cb9696882f219a7641
Source dataset
uspto-grants-2000_05
Patent number
US06057264

Reaction notes

Loading…