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

HRID 860705Notes

Reaction equation

HRID 860705 reaction equation
[C:1]1(=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=2)[CH:10]=[CH:9]1.C[O-].[Na+]>CO>[C:1]1([C:10]2[C:11]3[C:16](=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=3)[NH:8][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 3

HCID 7967CyclohexanoneHCID 5952301H-indole-6-carboxylic acidHCID 10942334Sodium Methoxide

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 mixture of 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. The resulting precipitate was collected by filtration, washed with cold water, and dried over phosphorous pentoxide (0.1 mm) to provide the desired product (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-46174ef65dba46de8bd946ddf81f006d
Source dataset
uspto-grants-2006_12
Patent number
US07153848B2

Reaction notes

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