Water → 1-Acetyl-5-chloroindoline

HRID 355098

Reaction equation

HRID 355098 reaction equation
[Cl:1]Cl.[C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)(=[O:5])[CH3:4].O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:1][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([C:3](=[O:5])[CH3:4])[CH2:7][CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 24526ChlorineHCID 276731-(2,3-Dihydro-1H-indol-1-yl)ethan-1-oneHCID 23665763Sodium Bisulfite

Product 1

HCID 123219901-Acetyl-5-chloroindoline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

74.5 g (1.05 moles) of chlorine were added with stirring at 20° to 30° C. to a mixture of 161 g (1 mole) of 1-acetyl-indoline in 1,050 ml of glacial acetic acid and the mixture was stirred for 15 minutes after which 8500 ml of water were added thereto with stirring. The mixture was stirred for 30 minutes and sodium bisulfite was added to destroy excess chlorine and was then vacuum filtered. The recovered product was dissolved in 250 ml of hot isopropanol and the mixture was cooled with stirring and then vacuum filtered. The product was rinsed with 250 ml of isopropanol to obtain 5-chloro-1-acetyl-indoline which was saponified as in Example 1 to obtain 70 g (45% yield) of 5-chloro-indoline.

Workup

  1. additionwere added
  2. stirringThe mixture was stirred for 30 minutes
  3. customto destroy excess chlorine
  4. filtrationvacuum filtered
  5. dissolutionThe recovered product was dissolved in 250 ml of hot isopropanol
  6. temperaturethe mixture was cooled
  7. stirringwith stirring
  8. filtrationvacuum filtered
  9. washThe product was rinsed with 250 ml of isopropanol

Sources & evidence

ORD record
ord-9a5fa3667cfc4917923de7021f293663
Source dataset
uspto-grants-1983_03
Patent number
US04377699

Linked notes

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