Dinitrofluorobenzene → N-(2,4-dinitrophenyl)-5-methyltryptamine

HRID 1837141Notes

Reaction equation

HRID 1837141 reaction equation
[CH3:1][C:2]1[CH:13]=[C:12]2[C:5]([NH:6][CH:7]=[C:8]2[CH2:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1F)([O-:21])=[O:20]>O.C(O)C>[N+:19]([C:22]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:23]=1[NH:11][CH2:10][CH2:9][C:8]1[C:12]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:13]=2)[NH:6][CH:7]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 157605-MethyltryptamineHCID 516892Sodium Bicarbonate

Product 1

HCID 9881070N-(2,4-dinitrophenyl)-5-methyltryptamineYield 85%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1 mMole of 5-metyltryptamine was dissolved in 100 ml of water and the pH was adjusted to pH 8.3 with 2.5 moles of sodium bicarbonate (NaHCO3), A 1.5% solution of 2,4-dinitrofluorobenzene in 200 ml ethanol was added and the mixture was stirred during 2 hours at room temperature. The desired product precipitates out, it is washed and dried. The product is obtained in 85% yield, and TLC (chloroform, silica-gel plates, reveals one yellow spot (Rf=0.8) which is well resolved from the starting materials under the same conditions.

Workup

  1. customThe desired product precipitates out
  2. washit is washed
  3. customdried
  4. customThe product is obtained in 85% yield, and TLC (chloroform, silica-gel plates

Sources & evidence

ORD record
ord-a2fbf7e83c0d46b6a343e10fb89c8769
Source dataset
uspto-grants-2004_08
Patent number
US06780884B2

Reaction notes

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