Acetyl chloride → 4-acetoxy-1-methyl-1H-indole-2-carboxylic acid

HRID 245736Notes

Reaction equation

HRID 245736 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[N:6]2[CH3:11].C(N(CC)CC)C.[C:22](Cl)(=[O:24])[CH3:23]>ClCCl>[C:22]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[N:6]2[CH3:11])(=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 102197584-Hydroxy-1-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 673629084-acetoxy-1-methyl-1H-indole-2-carboxylic acidYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-hydroxy-1-methyl-1H-indole-2-carboxylic acid (0.262 mmol, 50 mg) in dichloromethane (1 ml) and triethylamine (2.62 mmol, 365 μl) at 0° C. was added acetyl chloride (0.266 mmol, 19 μl) and the reaction mixture stirred at room temperature for one hour. The reaction was quenched with saturated aqueous sodium hydrogencarbonate and extracted twice with dichloromethane. The organic layers were combined, dried (Na2SO4) and concentrated under reduced pressure to yield 4-acetoxy-1-methyl-1H-indole-2-carboxylic acid (67 mg).

Workup

  1. customThe reaction was quenched with saturated aqueous sodium hydrogencarbonate
  2. extractionextracted twice with dichloromethane
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d3f9f3f14d404d4a862816a3b87e9b2b
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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