2-Hydrazinyl-4-methylquinoline → N-(2,6-Dichloropyridin-4-yl)-2-(4-methylquinolin-2-yl)hydrazinecarboxamide

HRID 2368700

Reaction equation

HRID 2368700 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH3:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:2].[Cl:14][C:15]1[CH:20]=[C:19]([N:21]=[C:22]=[O:23])[CH:18]=[C:17]([Cl:24])[N:16]=1>>[Cl:14][C:15]1[CH:20]=[C:19]([NH:21][C:22]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH3:13])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[N:4]=2)=[O:23])[CH:18]=[C:17]([Cl:24])[N:16]=1

Participants

3

Reactant 2

HCID 8181952-Hydrazinyl-4-methylquinolineHCID 27816582,6-Dichloro-4-isocyanatopyridine

Product 1

HCID 52912062N-(2,6-Dichloropyridin-4-yl)-2-(4-methylquinolin-2-yl)hydrazinecarboxamide

Procedure

A solution of 2-hydrazinyl-4-methylquinoline (100 mg, 0.58 mmol) and 110 mg (1.0 eq) of 2,6-dichloro-4-isocyanatopyridine was reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 2.57 (s, 3 H) 6.80 (s, 1 H) 7.30 (t, J=7.47 Hz, 1 H) 7.50-7.64 (m, 2 H) 7.87 (d, J=8.20 Hz, 1 H) 8.78 (s, 1 H) 8.91 (br. s., 1 H).

Sources & evidence

ORD record
ord-8996ebba65404129bef1d59d9b1fe9e2
Source dataset
uspto-grants-2014_04
Patent number
US08703797B2

Linked notes

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