8-Hydroxyquinoline → HCID 10364569, compound

HRID 1454011Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=[O:15])[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[OH:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]=[CH:24][CH:23]=[CH:22]2.N1CCOCC1>>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:18]3[C:17](=[C:26]4[N:25]=[CH:24][CH:23]=[CH:22][C:21]4=[CH:20][CH:19]=3)[O:16][CH:14]([OH:15])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

Participants

Reactant 3

HCID 19238-Hydroxyquinoline

HCID 8083Morpholine

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

Product 1

HCID 10364569HCID 10364569, compoundYield 34%

Procedure

The title compound was prepared following the procedure as in Example 18 from 3-(3-bromo-4,5-dimethoxyphenyl)-propenal (25 mg; 0.09 mmol) and 8-hydroxyquinoline (9 mg; 0.06 mmol) using morpholine (10 μl; 0.11 mmol) as base (yield: 34%). 1H NMR (acetone-d6): 8.85 (overlapping dd, J=1.8, 4.3 Hz; 1H), 8.20 (overlapping dd, J=1.8, 8.4 Hz; 1H), 7.47 (dd, J =4.1, 8.2 Hz, 1H), 7.34 (d, J=8.4 Hz) and 7.32 (d, J=8.4 Hz) (1H), 7.08 (d, J=2.1 Hz), 7.06 (d, J=2.1 Hz) and 7.05 (d, J=2.0 Hz) (2H), 6.98 (d, J=8.8 Hz) and 6.95 (d, J=8.8 Hz) (1H), 5.91 (t, J=2.7 Hz) and 5.70-5.72 (m) (1H), 4.50 (overlapping dd, J=6.3, 10.7 Hz; 1H), 3.85, 3.82, 3.81 and 3.80 (s each, 6H), 2.50-2.56 (m) and 2.20-2.37 (m) (2H).

Sources & evidence

ORD record: ord-a6621c727658441a8a9b1002b94b7c1a
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07476741B2

Reaction notes

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