Formaldehyde → 4-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-1H-indol-5-ol

HRID 2423118Notes

Reaction equation

HRID 2423118 reaction equation
[CH2:1]=O.[CH3:3][NH:4][CH2:5][CH2:6][OH:7].[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2>C(O)C>[OH:7][CH2:6][CH2:5][N:4]([CH2:1][C:10]1[C:9]([OH:8])=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)[CH3:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 80162-(Methylamino)ethanolHCID 160545-Hydroxyindole

Product 1

HCID 672405814-{[(2-Hydroxy-ethyl)-methyl-amino]-methyl}-1H-indol-5-olYield 100.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Paraformaldehyde (0.060 g, 2 mmol) and 2-methylamino ethanol (0.15 g, 2.0 mmol) was suspended in ethanol (10 mL) and heated at 50° C. for 20 minutes. The solution was cooled to room temperature and 5-hydroxyindole (0.27 mg, 2.0 mmol) was added. The solution was stirred under an atmosphere of N2 at room temperature overnight. The solution was evaporated to give the title compound (441 mg) that was used in the next step without further purification. MS m/z 221 [M+H]+.

Workup

  1. temperatureThe solution was cooled to room temperature
  2. customThe solution was evaporated

Sources & evidence

ORD record
ord-da6e1fe7a18148c385df0cd539ad48a9
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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