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

HRID 535367Notes

Reaction equation

HRID 535367 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)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 3,3-dimethyl-6-nitroindoline (450 mg) 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 rt overnight and quenched by addition of sat. aq. NaHCO3, and extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated. The residue was purified by column to give a light yellow solid (390 mg, 71% for two steps).

Workup

  1. customquenched by addition of sat. aq. NaHCO3
  2. extractionextracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column
  7. customto give a light yellow solid (390 mg, 71% for two steps)

Sources & evidence

ORD record
ord-d77186d683d94322b34e209109a71747
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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