Cyclohexanone → 3-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

HRID 747932Notes

Reaction equation

HRID 747932 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18]([OH:20])=[O:19])[CH:12]=2.C[O-].[Na+]>CO>[C:1]1([C:17]2[C:16]3[C:11](=[CH:12][C:13]([C:18]([OH:20])=[O:19])=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 10942334Sodium MethoxideHCID 126208262-Methyl-1H-indole-6-carboxylic acid

Product 1

HCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclohexanone (96 mL, 0.926 mol) was added to a stirred solution of methyl indole-6-carboxylic acid (50.0 g, 0.335 mol) in methanol (920 mL) at 22° C. Methanolic sodium methoxide (416 mL of 25% w/w, 1.82 mol) was added in portions over 10 minutes. The mixture was stirred at reflux for 18 hours, cooled to room temperature, concentrated, diluted with cold water, and acidified with 36% HCl solution. The resulting precipitate was collected by filtration, washed with cold water, and dried over phosphorous pentoxide (0.1 mm) to provide the title compound as a tan colored solid (80.9 g, 97.5% yield).

Workup

  1. temperatureat reflux for 18 hours
  2. concentrationconcentrated
  3. additiondiluted with cold water
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with cold water
  6. dry with materialdried over phosphorous pentoxide (0.1 mm)

Sources & evidence

ORD record
ord-d36c803bf19e4e179ee9693161a7e5ec
Source dataset
uspto-grants-2008_07
Patent number
US07399758B2

Reaction notes

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