Methyl p-toluenesulfonate → HCID 18995343, compound

HRID 374725Notes

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH+:2]=1.[C:11]1([CH3:22])[CH:16]=[CH:15][C:14]([S:17]([O:20]C)(=[O:19])=[O:18])=[CH:13][CH:12]=1>CO>[C:5]1([CH3:4])[C:10]([S:17]([O-:20])(=[O:19])=[O:18])=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:3][N+:2]1[CH2:1][CH2:10][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound was prepared using the procedure described by Koelsch et al in J. Am. Chem. Soc. (1953) 75, 2095. In a 250-ml one-necked round-bottomed flask equipped with a magnetic stir bar and a reflux condenser were placed 3,4-dihydroisoquinolinium (8.27 grams, 63 mmol) and 40 ml of methanol. The mixture was stirred and cooled to 0° C. A solution of methyl p-toluenesulfonate (11.73 g, 63 mmol) and 70 ml of methanol was added dropwise. The color of the solution remained clear and yellow. The mixture was heated to reflux for 6 hours. The methanol was then removed in vacuo to provide a quantitative yield (20 g) of an off-white solid (mp 115°-119° C.). The solid was pulverized and washed with 40 ml of acetone at room temperature. Suction filtration provided a white solid in 88% yield: mp 124°-127° C. 1H NMR (D2O): δ 2.27 (s,3H), 3.15 (t,2H), 3.73 (S,3H), 3.93 (t,2H), 7.18 (m,8H), 8.77 (s, 1H). Impurities observed at 4.46 (s), 8.0-8.3 (m), 9.4 (s) were due to N-methyl-isoquinoline p-toluenesulfonate.

Workup

customIn a 250-ml one-necked round-bottomed flask equipped with a magnetic stir bar and a reflux condenser
temperatureThe mixture was heated
temperatureto reflux for 6 hours
customThe methanol was then removed in vacuo

Sources & evidence

ORD record: ord-2de3aa09f4604bb4bfaa16161fc3a026
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05482515

Reaction notes

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