Methyl iodide → HCID 86751462, compound

HRID 1490276Notes

Reaction equation

HRID 1490276 reaction equation
[CH:1]1[C:17]2[C:16]([C:18]([O:20][CH3:21])=[O:19])=[C:15]3[C:7](=[C:8]4[C:13](=[N:14]3)[CH:12]=[CH:11][CH:10]=[CH:9]4)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:22][I:23]>>[IH:23].[CH3:22][NH+:6]1[C:7]2[C:15]([N:14]=[C:13]3[C:8]=2[CH:9]=[CH:10][CH:11]=[CH:12]3)=[C:16]([C:18]([O:20][CH3:21])=[O:19])[C:17]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 178496862HCID 178496862, compound

Product 1

HCID 86751462HCID 86751462, compoundYield 25%

Procedure

A solution of methyl quindoline-11-carboxylate (0.16 g, 0.58 mmol) from Example 15 in methyl iodide (3 mL, 30.2 mmol) was stirred at rt for 48 hours. The excess of CH3I was removed in vacuo and the residue was washed thoroughly with diethyl ether to afford the 0.06 g (25.0%) of the title compound as a red solid, mp 246.5°-247.0° C.; 1H NMR (DMSO-d6) δ 12.70 (s, 1H, NH), 8.92-8.80 (m, 3H), 8.22 (t, J=8.0, 1H), 8.09-7.95 (m, 2H), 7.94 (d, J=8.0, 1H), 7.58 (t, J=7.6, 1H); 13C NMR (DMSO-d6) δ 164.01, 146.47, 141.01, 135.35, 135.14, 132.10, 131.94, 128.40, 126.89, 126.37, 122.88, 122.09, 118.60, 113.86, 113.54, 95.02, 54.20, 41.29; MS (LSIMS, m/z) 291 (M+).

Workup

  1. customThe excess of CH3I was removed in vacuo
  2. washthe residue was washed thoroughly with diethyl ether

Sources & evidence

ORD record
ord-c54159a31ba641da8bf64202a14a34e7
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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