Morpholine → Methanol

HRID 1454013Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[Br:11][C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=[O:25])[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].N1CC[O:29][CH2:28]C1>>[Br:11][C:12]1[CH:13]=[C:14]([CH:22]2[C:3]3[C:2](=[C:10]4[NH:9][CH:8]=[CH:7][C:6]4=[CH:5][CH:4]=3)[O:1][CH:24]([OH:25])[CH2:23]2)[CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19].[CH3:28][OH:29]

Participants

Reactant 3

HCID 8083Morpholine

HCID 27376517-Hydroxyindole

HCID 858878623-(3-Bromo-4,5-dimethoxyphenyl)-propenal

Product 2

HCID 887MethanolYield 20%

HCID 11741932HCID 11741932, compound

Procedure

The title compound was prepared following the procedure as in Example 18 from 7-hydroxy-indole (0.200 g, 1.50 mmol) and 3-(3-bromo-4,5-dimethoxyphenyl)-propenal (0.416 g, 1.50 mmol) using morpholine (0.143 mL, 1.65 mmol) as a base in refluxing methanol (7.5 mL) (yield: 20%). 1H NMR (CDCl3): 10.22 and 10.16 (s each, 1H); 7.27-7.24 (m, 1H); 7.03-6.94 (m, 3H); 6.42-6.36 (m, 2H); 6.21 (d, J=7.6 Hz) and 6.16 (dd, J=5.0, 1.0 Hz) (1H); 5.74-5.71 and 5.61-5.56 (m each, 1H); 4.42-4.36 (m, 1H); 3.83 (s, 3H); 3.79 (s, 3H); 2.85-2.48 and 2.28-2.09 (m each, 2H).

Sources & evidence

ORD record: ord-339db761ce7b4d24807e80eeabced01a
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476741B2

Reaction notes

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