Quinoline → HCID 86624614, compound

HRID 1160093Notes

Reaction equation

HRID 1160093 reaction equation
[N:1]1[C:10]2C(=C[CH:7]=[CH:8][CH:9]=2)C=CC=1.[Br-:11].[CH3:12][O:13][N:14]=[C:15]([C:23]1[CH:28]=[CH:27][C:26](C)=[CH:25][CH:24]=1)[CH2:16][N+:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[Br-:11].[CH3:12][O:13][N:14]=[C:15]([C:23]1[CH:24]=[CH:25][C:26]([N:1]2[CH2:7][CH2:8][CH2:9][CH2:10]2)=[CH:27][CH:28]=1)[CH2:16][N+:17]1[C:18]2[C:19](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 73128258HCID 73128258, compound

Product 1

HCID 86624614HCID 86624614, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of quinoline (149 μl, 1.26 mmol) and (8) (486 mg, 1.64 mmol) was refluxed in acetone (4 mL) for 5 days. A dark red solid was separated by filtration in 61% yield: mp 178-180° C.; 1H NMR 400 MHz (DMSO-d6) δ 1.90 (s, 4H), 3.15 (s, 4H), 3.99 (s, 3H), 6.39 (m, 4H), 7.36 (d, 2H, J=7.3 Hz), 8.05 (t, 1H, J=7.0 Hz), 8.18 (m, 1H), 8.30 (m, 2H), 8.46 (d, 1H, J=8.1 Hz), 9.29 (d, 1H, J=8.1 Hz), 9.65 (d, 1H, J=5.1 Hz); FABHRMS: found M+, 346.1920 (calcd for C22H24ON3: M+, 346.1914).

Workup

  1. customA dark red solid was separated by filtration in 61% yield

Sources & evidence

ORD record
ord-6916d1d494e34ea4b3123d9256635c56
Source dataset
uspto-grants-2010_10
Patent number
US07816352B2

Reaction notes

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