Acetyl chloride → HCID 22217727, compound

HRID 277726Notes

Reaction equation

HRID 277726 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1C.[CH2:12](N(CC)CC)C.[C:19](Cl)(=[O:21])[CH3:20]>ClCCl>[C:19]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][C:2]1([CH3:1])[CH3:12])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 583485dimethylindoline

Product 1

HCID 22217727HCID 22217727, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of dimethyl indoline (65 mg, 0.44 mmol) and triethylamine (0.12 mL, 0.88 mmol) in dry dichloromethane (3 mL) was treated with acetyl chloride (0.05 mL, 0.66 mmol) at 0° C. The mixture was allowed to warm to room temperature and was stirred for 16 h. Then the reaction mixture was quenched with water and the product was extracted into ether. The organic layer was washed with water and brine, dried (sodium sulfate) filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluent: 30% EtOAc in hexanes) to give N-acetyl dimethyl indoline as a light yellow oil (68 mg, 82%).

Workup

  1. customThen the reaction mixture was quenched with water
  2. extractionthe product was extracted into ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel (eluent: 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5f33665a38a242e28ad4444e2d7236eb
Source dataset
uspto-grants-2002_03
Patent number
US06358945B1

Reaction notes

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