Acetyl chloride → 1-(6-Nitroindolin-1-yl)ethanone

HRID 907177Notes

Reaction equation

HRID 907177 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CCN(CC)CC.[C:20](Cl)(=[O:22])[CH3:21]>C1COCC1>[C:20]([N:10]1[C:11]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=2)[CH2:8][CH2:9]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 297576-Nitroindoline

Product 1

HCID 2585661-(6-Nitroindolin-1-yl)ethanoneYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Nitroindoline (3.0 g, 18.3 mmol) was dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at 0° C. Acetyl chloride (1.5 mL, 21 mmol) was added dropwise. The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated to yield 1-acetyl-6-nitroindoline (3.8 g, 100%) as a yellow solid.

Workup

  1. customat 0° C
  2. customThe mixture was partitioned between EtOAc and aqueous HCl
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3971a915551b4b56a3e6d6cfd651cbcd
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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