Dimedone → 4,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acid

HRID 1372395Notes

Reaction equation

HRID 1372395 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][C:7]([OH:9])=[O:8].[CH3:11][C:12]1([CH3:20])[CH2:17][C:16](=[O:18])[CH2:15][C:14](=O)[CH2:13]1.C([O-])(=O)C.[Na+]>O>[CH3:11][C:12]1([CH3:20])[CH2:13][C:14]2[NH:2][CH:3]=[C:4]([CH2:5][CH2:6][C:7]([OH:9])=[O:8])[C:15]=2[C:16](=[O:18])[CH2:17]1

Participants

5

Reactant 3

HCID 31358DimedoneHCID 123608Aminolevulinic Acid HydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 210718994,5,6,7-H4-6,6-Me2-4-oxo-indole-3-propanoic acidYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 5-aminolevulinic acid hydrochloride (1.68 g, 10 mmol), 5,5-dimethyl-1,3-cyclohexandione (1.4 g, 10 mmol) and sodium acetate (1.64 g, 20 mmol) in water (10 mL) was heated to at 110° C. for 4 hours and then cooled. The resulting solid was collected by vacuum filtration, washed with 30% ethanol in water and dried under vacuum to give 1.6 g (68% yield) of 3-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydro-1H-indol-3-yl)-propionic acid. 1H-NMR (360 MHz, dimethylsulfoxide-d6) δ 11.89 (br s, 1H, COOH), 10.94 (br s, 1H, NH), 6.45 (d, 1H), 2.76 (t, 2H, CH2), 2.57 (s, 2H, CH2), 2.44 (t, 2H, CH2), 2.16 (s, 2H, CH2), 0.99 (s, 6H, 2×CH3). MS m/z 235 [M+].

Workup

  1. temperaturecooled
  2. filtrationThe resulting solid was collected by vacuum filtration
  3. washwashed with 30% ethanol in water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-8c61c98a8fb04eb4b5e756207e665d50
Source dataset
uspto-grants-2007_01
Patent number
US07157577B2

Reaction notes

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