1,2-Cyclohexanedione → 3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acid

HRID 1836119Notes

Reaction equation

HRID 1836119 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][C:7]([OH:9])=[O:8].C([O-])(=O)C.[Na+].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=[O:22]>O>[O:22]=[C:17]1[CH2:18][CH2:19][CH2:20][C:21]2[NH:2][CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:16]1=2

Participants

5

Reactant 3

HCID 130061,2-CyclohexanedioneHCID 123608Aminolevulinic Acid HydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acidYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Aminolevulinic acid hydrochloride salt (13.7 g, 0.1 mol), sodium acetate (41 g, 0.2 mol), and 1,2-cyclohexanedione (11.2 g, 0.1 mol) were stirred for 20 hours in 200 ml of water at 50° C. The mixture was cooled and the solid product collected by vacuum filtration and washed with 50% ethanol in water. The product was slurry-washed in 100 ml of 50% ethanol in water, collected and dried under vacuum to give 3-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propionic acid (12 g, 67% yield).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe solid product collected by vacuum filtration
  3. washwashed with 50% ethanol in water
  4. washThe product was slurry-washed in 100 ml of 50% ethanol in water
  5. customcollected
  6. customdried under vacuum

Sources & evidence

ORD record
ord-d18f66590a3448c18781c781bc0df41a
Source dataset
uspto-grants-2004_08
Patent number
US06777417B2

Reaction notes

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