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

HRID 1009607Notes

Reaction equation

HRID 1009607 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) is dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at 0° C. Acetyl chloride (1.5 mL, 21 mmol) is added dropwise. The mixture is stirred at room temperature for 30 minutes. The mixture is partitioned between EtOAc and aqueous HCl. The organic layer is 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 is partitioned between EtOAc and aqueous HCl
  3. customThe organic layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bfbc52f233ea43279c5d24fdea560e8a
Source dataset
uspto-grants-2011_07
Patent number
US07973069B2

Reaction notes

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