Methyl iodide → HCID 21481068, compound

HRID 1490289Notes

Reaction equation

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

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 67598756HCID 67598756, compound

Product 1

HCID 21481068HCID 21481068, compoundYield 27%

Conditions

Temperature: 150 °C

Procedure

6-Methoxy-10-acetylquindoline from Example 36 (194 mg, 0.668 mmol) was suspended in CH3I (1.25 mL, 200 mmol) and heated in a pressure vessel at 150° C. with stirring for 24 h. After cooling, the resulting precipitate was filtered and dried to obtain 77 mg (27%) of the title compound as brown crystals, mp >250° C. (sublimes); 1H NMR (DMSO-d6) 9.84 (s, 1H), 8.83 (d, J=8.0, 1H), 8.56 (d, J=8.8, 1H), 8.22 (m, 1H), 8.09 (m, 1H), 7.94 (t, J=8.0, 1H), 7.79 (m, 2H), 5.07 (s, 3H), 4.17 (s, 3H), 3.06 (s, 3H); 13C NMR (DMSO-d6) δ 170.5, 150.8, 143.7, 143.1, 135.5, 132.5, 130.1, 129.3, 129.12, 129.09, 127.5, 125.1, 122.3, 117.5, 116.8, 115.2, 57.3, 47.7, 27.7; MS (LSIMS, m/z) 305 (M+).

Workup

temperatureAfter cooling
filtrationthe resulting precipitate was filtered
customdried

Sources & evidence

ORD record: ord-bafa9dd3f00a4f099cd8faeb1fabbc24
Source dataset: uspto-grants-1997_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05681958

Reaction notes

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