Water → HCID 13574130, compound

HRID 2195733Notes

Reaction equation

HRID 2195733 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:9][O:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([CH:17]=[CH:18][NH:19]2)=[CH:15][CH:14]=1)=[O:12].O>C(Cl)Cl>[CH3:9][O:10][C:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17]([C:1](=[O:3])[CH3:2])=[CH:18][NH:19]2)=[CH:15][CH:14]=1)=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 639844Methyl indole-6-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 13574130HCID 13574130, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acetyl chloride (0.23 mL, 3.3 mmole) and aluminum chloride (0.88 g, 6.6 mmol) in methylene chloride (30 mL) was added 1H-indole-6-carboxylic acid methyl ester (0.53 g, 3.0 mmol). After stirring 1 hr at room temperature water (300 mL) was added and then this was extracted with ethyl acetate (300 mL). The organic layer was dried (MgSO4), filtered and concentrated to collect 0.65 g (99% yield) of 3-acetyl-1H-indole-6-carboxylic acid methyl ester a light yellow solid. 1H NMR (300 MHz, DMSO) a 12.27 (s, 1H), 8.52 (s, 1H), 8.24 (d, 1H, J=8.2 Hz), 8.08 (d, 1H, J=1.0 Hz), 7.78 (dd, 1H, J=8.2, 1.0 Hz), 3.86 (s, 3H), 2.47 (s, 3H).

Workup

  1. additionwas added
  2. extractionthis was extracted with ethyl acetate (300 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-81331ca94ee14371bcfcf6cb49b83ee9
Source dataset
uspto-grants-2012_12
Patent number
US08338416B2

Reaction notes

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