Acetyl chloride → 1-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanone

HRID 971256Notes

Reaction equation

HRID 971256 reaction equation
[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[NH:4][CH2:3]1.[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl.CCN(CC)CC>[CH3:1][C:2]1([CH3:14])[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([C:15](=[O:17])[CH3:16])[CH2:3]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 219594663,3-Dimethyl-6-nitroindoline

Product 1

HCID 161274181-(3,3-Dimethyl-6-nitroindolin-1-yl)ethanoneYield 72.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 3,3-dimethyl-6-nitroindoline (450 mg, 2.3 mmol) in CH2Cl2 (15 mL) and Et3N (0.6 mL) at −10° C. was added acetyl chloride (180 μL, 2.5 mmol). The mixture was stirred at room temperature overnight, quenched by adding saturated aqueous sodium bicarbonate, and extracted with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), and evaporated. The residue was purified by flash chromatography over silica gel to give a light yellow solid (390 mg).

Workup

  1. customquenched
  2. additionby adding saturated aqueous sodium bicarbonate
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-6948814f64cf43b5bea346846a18ab1e
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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