Methyl iodide → HCID 86751457, compound

HRID 1490265Notes

Reaction equation

HRID 1490265 reaction equation
[CH:1]1[C:17]2[CH:16]=[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.[CH3:18][I:19]>CO>[IH:19].[CH3:18][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)=[CH:16][C:17]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]1=2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178420006HCID 178420006, compound

Product 1

HCID 86751457HCID 86751457, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of quindoline (2.0 g, 9.2 mmol) from Example 2, methanol (5 mL) and methyl iodide (880 mL, 14.1 mmol) was heated in a bomb at 120° C. for 4 hours. After cooling, the resulting brown precipitate (2.5 g, 75.5%) was filtered and washed with ether. Recrystallization from water gave the title compound as bright yellow crystals, yield 50%, mp 283.5°-284° C. [lit 284°-286° C. (Gellert, E.; Raymond-Hamet; Schlittler, E. Helv. Chim. Acta 1951, 34, 642-651)]; 1H NMR (DMSO-d6) δ 12.87 (s, 1H, NH), 9.28 (s, 1H, H11), 8.79 (d, J=8.4, 1H, H6), 8.75 (d, J=9.2, 1H, H4), 8.57 (d, J=8.3, 1H, H1), 8.16 (t, J=7.6, 1H, H3), 7.94-7.92 (dd, J=7.2, J=7.0, 2H, H2 and H8), 7.82 (d, J=8.4, 1H, H9), 7.51 (t, J=7.0, 1H, H7), 5.02 (s, 3H, NCH3); 13C NMR (DMSO-d6) δ 145.62, 137.97, 135.25, 133.87, 133.16, 132.34, 129.76, 126.99, 126.21, 126.13, 124.72, 121.31, 117.78, 113.76, 113.10, 40.19; MS (EI, m/z) 232.1 (M+) .

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting brown precipitate (2.5 g, 75.5%) was filtered
  3. washwashed with ether
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-027f71479eb4408ab2be0f22435ac0a8
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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