Pyridine → 6-Fluoromelatonin

HRID 371683Notes

Reaction equation

HRID 371683 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][C:4]=1[F:15].N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:14]=[C:13]2[C:6](=[CH:5][C:4]=1[F:15])[NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH:12][C:22](=[O:24])[CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 601383HCID 601383, compound

Product 1

HCID 439226-FluoromelatoninYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.75 grams (3.6 mmole) of the tryptamine, 2.0 ml. of pyridine, and 8.0 ml. of benzene was prepared. Acetic anhydride (1.0 ml.) was slowly added. The mixture was stirred at room temperature for 4 hours, and the solvents then were removed in vacuo with moderate heating. The resulting crystalline residue was dissolved in a 1:1 mixture of warm ethyl acetate and chloroform. The solution was washed with water, then with sodium chloride solution, and then dried over sodium sulfate. The solvents were removed in vacuo. The crystalline residue was boiled in benzene for a few minutes. The mixture was allowed to stand at room temperature for several hours, and the resulting product was collected by filtration and dried to obtain 0.81 grams (90 percent) of N-[2-(5-methoxy-6-fluoroindol-3-yl)ethyl]acetamide, m.p. 158°-159° C.

Workup

  1. customthe solvents then were removed in vacuo with moderate heating
  2. dissolutionThe resulting crystalline residue was dissolved in a 1:1 mixture of warm ethyl acetate and chloroform
  3. washThe solution was washed with water
  4. dry with materialwith sodium chloride solution, and then dried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. waitThe crystalline residue was boiled in benzene for a few minutes
  7. waitto stand at room temperature for several hours
  8. filtrationthe resulting product was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-d11f430c68b14b299614f1cf3bee9885
Source dataset
uspto-grants-1978_05
Patent number
US04087444

Reaction notes

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