Methyl iodide → HCID 44326150, compound

HRID 1490274Notes

Reaction equation

HRID 1490274 reaction equation
[CH3:1][N:2]1[C:18]2[C:17]([C:19]([O:21][CH3:22])=[O:20])=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]3)=[N:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[CH3:23][I:24]>>[I-:24].[CH3:23][N+:10]1[C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:2]([CH3:1])[C:18]=2[C:17]([C:19]([O:21][CH3:22])=[O:20])=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2

Participants

3

Reactant 2

HCID 6328Methyl iodideHCID 14366447HCID 14366447, compound

Product 1

HCID 44326150HCID 44326150, compound

Procedure

A solution of methyl 10-methylquindoline-11-carboxylate (0.5 g, 1.72 mmol) from Example 13 in methyl iodide (5 mL, 50.3 mmol) was stirred at room temperature for 48 hours. The excess of CH3I was removed in vacuo and the residue was dissolved in MeOH (10 mL). Diethyl ether (30 mL) was added and the precipitate was filtered and washed thoroughly with diethyl ether to afford, after drying, 0.33 g (44.6%) of the title compound as an orange solid, mp 257.0°-257.5° C. (decomp.); 1H NMR (DMSO-d6) δ 8.90 (dd, J=2.8, J=9.2, 2H), 8.33 (d, J=8.0, 1H), 8.24 (t, J=6.8, 1H), 8.10 (t, J=5.2, 2H), 8.04 (t, J=8.4, 1H), 7.62 (t, J=8.0, 1H), 5.08 (s, 3H), 4.31 (s, 3H), 3.99 (s, 3H); 13C NMR (DMSO-d6) δ 164.95, 148.00, 140.47, 135.11, 134.96, 132.61, 129.99, 128.74, 126.96, 125.76, 124.86, 122.31, 122.27, 118.72, 113.60, 111.71, 54.67, 41.20, 30.98; MS (LSIMS, m/z) 305 (M+).

Workup

  1. customThe excess of CH3I was removed in vacuo
  2. dissolutionthe residue was dissolved in MeOH (10 mL)
  3. additionDiethyl ether (30 mL) was added
  4. filtrationthe precipitate was filtered
  5. washwashed thoroughly with diethyl ether
  6. customto afford
  7. customafter drying

Sources & evidence

ORD record
ord-2a7eb8e21f1a47e7b6191c37f3b4317f
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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