Potassium Carbonate → 2-(2-(5-hydroxy-1H-indol-3-yl)ethyl)isoindole-1,3-dione

HRID 964758Notes

Reaction equation

HRID 964758 reaction equation
CN1C(N)=NC(=O)C1.[CH:9]1[C:14]([OH:15])=[CH:13][C:12]2[C:16]([CH2:19][CH2:20][NH2:21])=[CH:17][NH:18][C:11]=2[CH:10]=1.O.OS(O)(=O)=O.C(N1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43])(OCC)=O.C(=O)([O-])[O-].[K+].[K+]>O>[OH:15][C:14]1[CH:13]=[C:12]2[C:11](=[CH:10][CH:9]=1)[NH:18][CH:17]=[C:16]2[CH2:19][CH2:20][N:21]1[C:37](=[O:38])[C:36]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:35]2[C:34]1=[O:43]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 164531Serotonin creatinine sulfate monohydrate

Product 1

HCID 7901972-(2-(5-hydroxy-1H-indol-3-yl)ethyl)isoindole-1,3-dioneYield 954.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of serotonin creatinine sulfate monohydrate (5 g, 12.333 mmol) in water (80 mL) were added N-carbethoxyphthalimide (2.84 g, 1.30 mmol) and potassium carbonate (3.54 g, 24.6 mmol). The resulting mixture was stirred at room temperature for 4 hours. The precipitate was filtered, washed with water and dried to give the title compound (3.8 g, 100%) as a yellow solid. 1H NMR (CD3SOCD3, 300 MHz) δ: 10.52 (s, 1H), 8.64 (s, 1H), 7.87-7.83 (A2B2 system, 4H), 7.12 (d, J=8.6 Hz, 1H), 7.08 (broad s, 1H), 6.89 (broad s, 1H), 6.60 (broad d, J=8.6 Hz, 1H).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-60207d3141fc4bc686a38d32873d4875
Source dataset
uspto-grants-1998_06
Patent number
US05770742

Reaction notes

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