Acetyl chloride → 1H-indole-2-carbonyl Chloride

HRID 1517013Notes

Reaction equation

HRID 1517013 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.C([Cl:16])(=O)C.P(Cl)(Cl)(Cl)(Cl)Cl>CCOCC>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([Cl:16])=[O:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24819Phosphorus pentachlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 118162081H-indole-2-carbonyl ChlorideYield 73.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 1H-Indole-2-carboxylic acid (2.50 g, 15.5 mmol) and acetyl chloride (31 mL, 0.43 mol) in Et2O (31.5 mL) was added phosphorus pentachloride (3.55 g, 17.1 mmol) in portions, and the mixture was then heated under reflux for 1.5 hours. The cooled reaction mixture was concentrated under reduced pressure, and the crude product obtained thus was recrystallized from heptanes to give 1H-indole-2-carbonyl chloride (2.04 g, 73%) as yellow needles.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux for 1.5 hours
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe crude product obtained thus
  6. customwas recrystallized from heptanes

Sources & evidence

ORD record
ord-beef6375891a4a8a9f9493d59d379939
Source dataset
uspto-grants-2012_07
Patent number
US08227486B2

Reaction notes

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