8-Hydroxyquinoline → HCID 4532562, compound

HRID 541024Notes

Reaction equation

[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1.[OH:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[N:27]=[CH:26][CH:25]=[CH:24]2>>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[CH:1]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=1)[C:20]1[C:19]([OH:18])=[C:28]2[C:23]([CH:24]=[CH:25][CH:26]=[N:27]2)=[CH:22][CH:21]=1

Participants

Reactant 3

HCID 19238-Hydroxyquinoline

HCID 6998Salicylaldehyde

HCID 157652-Amino-6-methylpyridine

Product 1

HCID 4532562HCID 4532562, compound

Procedure

The title compound was prepared by method B presented for the compound of Example 1 with the change that the reaction was conducted with salicylaldehyde (Molar), 2-amino-6-picoline (1 equivalent) and 8-hydroxy-quinoline (0.6 equivalent) as starting materials. Product precipitation; C22H19N3O2; (MW: 357.1), yield 1.6 g, (50.9%); m.p.: 189-191° C.; HPLC (CH3CN/H2O 70.30 Phenomenex C18 282 nm): Tr=5.05 min. 1H NMR 13 (DMSO) δ 2.23 (3H, s), 6.34 1H, d, J=6.0 Hz), 6.38 (1H, d, J=7.1 Hz), 6.69 (1H, t, J=7.2 Hz), 6.80 (2H, m) 7.02 (2H, m), 7.18 (1H, d, J=6.2 Hz), 7.25 (1H, d, J=6.8 Hz), 7.36 (1H, d, J=7.4 Hz), 7.42-7.54 (1H, m), 7.64 (1H, d, J=7.9 Hz), 8.25 (1H, d, J=7.1 Hz), 8.80 (1H, s), 9.85 (1H, s) —C NMR 13 (DMSO) δ 23.9 (CH3), 47.8 (CHNH), 111.1 (CH), 115.7 (CH), 116.7 (CH), 118.7 (CH), 121.5 (CH), 125.3 (Cq), 127.2 (CH), 127.4 (Cq), 127.8 (CH), 128.3 (CH), 129.2 (Cq), 135.9 (CH), 137.5 (CH), 138.2 (Cq), 148.1 (CH), 149.7, 155.1, 155.6 and 157.6 (4×Cq).

Workup

customProduct precipitation
customTr=5.05 min

Sources & evidence

ORD record: ord-250c645ad095477e87feefca61093564
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871937B2

Reaction notes

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