Methyl iodide → HCID 9842782, compound

HRID 2255917Notes

Reaction equation

HRID 2255917 reaction equation
[N:1]1([C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([NH:17][CH3:18])[CH:11]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:19][I:20]>O1CCOCC1>[I-:20].[CH3:19][N+:13]1[C:14]([CH3:16])=[CH:15][C:10]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:11][C:12]=1[NH:17][CH3:18]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 190290604-(1H-Indol-1-yl)-N,6-dimethylpyridin-2-amine

Product 1

HCID 9842782HCID 9842782, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(1-indolyl)-6-methyl-2-methylaminopyridine (0.35 g, 1.48 mM), methyl iodide (0.5 ml) and dioxane (20 ml) was heated at 90° C. for 15 hours. The mixture was cooled. The solid was collected by filtration, washed with dioxan (10 ml) and then recrystallised from methanol. There was thus obtained 1,6-dimethyl-4-(1-indolyl)-2-methylaminopyridinium iodide (0.15 g, 27% yield), m.p. 275°-277° C.; microanalysis, found: C,49.3; H,4.7; N,10.3%; C16H18N3I. 0.5H2O requires: C,49.5; H,4.9; N,10.8%; NMR: 2.66(3H,s,CH3), 3.1(3H,d, NHCH3), 3.67(3H,s,N+CH3), 6.9(1H,d, indole-3H), 7.05(1H,d,pyridine-3H), 7.2-7.4(3H, complex, pyridine 5-H and aromatic), 7.7(1H,d, aromatic), 7.9-8.0(2H, complex, aromatic and indole-2H), 8.15-8.25(1H,br,NH).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationThe solid was collected by filtration
  3. washwashed with dioxan (10 ml)
  4. customrecrystallised from methanol

Sources & evidence

ORD record
ord-f3f86af6b179483dbbdf5ee2846fb504
Source dataset
uspto-grants-1997_08
Patent number
US05654298

Reaction notes

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