Methyl iodide → 5-Methoxybenzoquinoline-n-propanesulfonic acid
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]3=2)[CH:4]=[CH:3][CH:2]=1.CN1C2C(=CC=C3C=CC=CC3=2)C=C[CH:17]1[OH:30].[CH2:31]1[CH2:37][S:34](=[O:36])(=[O:35])[O:33][CH2:32]1.CI>>[CH3:17][O:30][C:6]1[CH:7]=[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]2=[C:10]2[C:5]=1[CH:4]=[CH:3][CH2:2][N:1]2[CH2:32][CH2:31][CH2:37][S:34]([OH:33])(=[O:36])=[O:35]Participants
Procedure
Compound 13 wae synthesized according to the procedure outlined above in Example 3 for the synthesis of the N-methyl-hydroxy benzoquinoline derivative 15. Compound 13 was then allylated according to the general amino group alkylation procedure described above in Example 3, this time using 1,3-propane sultone as the alkylating agent rather than MeI, to give a 5-methoxybenzoquinoline-N-propanesulfonic acid intermediate 16 (1HNMR: CD3OD d 7.94 (d, 1 H, J=8.7 Hz), 7.65 (d, 1 H, J=8.4 Hz), 7.32 (t, 1 H), 7.27 (t, 1 H), 6.85 (s, 1 H), 4.89 (s, 3 H), 3.20 (m, 2 H), 3.08 (bt, 2 H, J=6 Hz), 2.91 (m, 2 H), 2.72 (t, 2 H, J =6.6 Hz), 2.33 (m, 2 H), 1.89 (m, 2 H). Subsequent methoxy group deprotection of compound 16 by the general boron tribromide procedure described above in Example 1 resulted in the 3-(5-hydroxybenzoquinolin-1-yl) propanesulfonic acid 17.
Sources & evidence
- ORD record
- ord-5f45cd3f3ab84c349076f4296115ad61
- Source dataset
- uspto-grants-2001_12
- Patent number
- US06326153B2
Reaction notes
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