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

HRID 597844Notes

Reaction equation

HRID 597844 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:11]1(=O)[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1.C([O-])(=O)C.[Na+]>O>[C:7]([CH2:6][CH2:5][C:4]1[C:12]2[C:13](=[O:17])[CH2:14][CH2:15][CH2:16][C:11]=2[NH:2][CH:3]=1)([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 123608Aminolevulinic Acid HydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 158327213-(4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)propanoic acidYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-aminolevulinic acid hydrochloride (2, 50.0 g, 0.298 mol), 1,3-cyclohexanedione (1, 40.2 g, 0.359 mol), and sodium acetate (48.8 g, 0.595 mol) was added with H2O (125 mL). The reaction mixture was heated at 100° C. for 16 h. The solution was cooled to room temperature and the resultant precipitate was filtered, washed with water (200 mL×2), and air-dried to give 3-carboxyethyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (3, 50.5 g, 0.245 mol) as yellow solids in 82% yield.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationthe resultant precipitate was filtered
  3. washwashed with water (200 mL×2)
  4. customair-dried

Sources & evidence

ORD record
ord-53c1c1acc91d450695e1610e37bd0dff
Source dataset
uspto-grants-2011_03
Patent number
US07897602B2

Reaction notes

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