7-Aminoquinoline → 3-Methyl-4-(4-pyridyl)-N-quinolin-7-ylbenzamide

HRID 494242Notes

Reaction equation

[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[C:16](O)=[O:17]>>[CH3:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=1[C:22]1[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=1)[C:16]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)=[O:17]

Participants

Reactant 2

HCID 113777-Aminoquinoline

HCID 227106613-Methyl-4-(pyridin-4-yl)benzoic acid

Product 1

HCID 576827353-Methyl-4-(4-pyridyl)-N-quinolin-7-ylbenzamide

Procedure

Using the procedure outlined in Example 56, the title compound was prepared from 7-aminoquinoline (D55) (25 mg, 0.17 mmol) and 3-methyl-4-(4-pyridyl)benzoic acid (D57) (44 mg, 0.21 mmol) as an orange solid. 1H NMR (400 MHz, CDCl3) δ (ppm): 8.91(dd, 1H), 8.70 (d, 2H), 8.22 (m, 2H), 8.14 (dd, 1H), 8.11 (dd, 1H), 7.84 (m, 3H), 7.36 (m, 2H), 7.28 (m, 2H), 2.37 (s, 3H).

Sources & evidence

ORD record: ord-351c506d168e4fbfac030bd645e35275
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538121B2

Reaction notes

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