Iodoethane → HCID 86751458, compound

HRID 1490267Notes

Reaction equation

HRID 1490267 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.[CH2:18]([I:20])[CH3:19]>>[IH:20].[CH2:18]([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)[CH3:19]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 178420006HCID 178420006, compound

Product 1

HCID 86751458HCID 86751458, compoundYield 87.7%

Conditions

Temperature
135 °C

Procedure

A suspension of quindoline (1 g, 4.6 mmol) from Example 2 and ethyl iodide (3 mL, 37.7 mmol) was heated in a bomb at 135° C. for 15 hours. The excess ethyl iodide was removed and the resulting brown precipitate was collected, washed with ether and dried, yielding 1.5 g (87.7%) of 5-ethylquindolinium hydroiodide. Recrystallization from water afforded bright yellow crystals of 5-ethylquindolinium hydroiodide, mp 256° C. [lit 222°-223° C. (Fichter, F.; Boehringer, R. Ber 1906, 3941)]; 1H NMR (DMSO-d6) δ 12.93 (s, 1H, NH), 9.32 (s, 1H, H11), 8.78 (d, J=9.2, 1H, H4), 8.66 (d, J=8.4, 1H, H6), 8.60 (d, J=8.0, 1H, H1), 8.18 (t, J=7.6, 1H, H3) , 7.95 (dd, J=8.0, J=7.2, 2H, H2 and H8) , 7.87 (d, J=8.4, 1H, H9), 7.55 (t, J=7.6, 1H, H7), 5.55 (q, J=6.8, 2H, NCH2), 1.76 (t, J=7.2, 3H, CH3); 13C NMR (DMSO-d6) δ 145.78, 136.92, 134.34, 133.94, 133.52, 132.71, 130.06, 127.09, 126.42, 125.50, 125.14, 121.81, 117.31, 113.35, 112.80, 47.33, 13.30; MS (EI, m/z) 246 (M+ -1)

Workup

  1. customThe excess ethyl iodide was removed
  2. customthe resulting brown precipitate was collected
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-cf725ad54c8548e588ce09ebaf8e3dfe
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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