5-Chloro-2-methylindole → 4-(5-Chloro-2-methyl-1H-indol-3-yl)-2,2-dimethyl-4-oxo-butyric acid

HRID 1013224Notes

Reaction equation

HRID 1013224 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:6][C:5](=[O:7])[O:4][C:3]1=[O:8].[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([CH3:20])=[CH:14]2.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCCl>[Cl:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15]([CH3:20])=[C:14]2[C:5](=[O:7])[CH2:6][C:2]([CH3:9])([CH3:1])[C:3]([OH:4])=[O:8]

Participants

5

Reactant 3

HCID 706365-Chloro-2-methylindoleHCID 870672,2-Dimethylsuccinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 673154144-(5-Chloro-2-methyl-1H-indol-3-yl)-2,2-dimethyl-4-oxo-butyric acid

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3,3-Dimethyl-dihydro-furan-2,5-dione (7.8 mmol, 1.0 g), 5-chloro-2-methylindole (13.8 mmol, 2.28 g), and AlCl3 (9.0 mmol, 1.2 g) were stirred in 100 mL DCE overnight at 65° C. The reaction was cooled and quenched with 10 mL water. The resultant precipitate was filtered and washed with a small amount of DCE giving 1.06 g of the sub-titled compound.

Workup

  1. temperatureThe reaction was cooled
  2. customquenched with 10 mL water
  3. filtrationThe resultant precipitate was filtered
  4. washwashed with a small amount of DCE giving 1.06 g of the sub-titled compound

Sources & evidence

ORD record
ord-fdea7c0e784241ecb857ce778f08894c
Source dataset
uspto-grants-2011_07
Patent number
US07981912B2

Reaction notes

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