3,5-Dichlorophenyl isocyanate → N-(3,5-Dichlorophenyl)-2-(4-isopropyl-5,8-dimethylquinolin-2-yl)hydrazinecarboxamide

HRID 1892266Notes

Reaction equation

HRID 1892266 reaction equation
[NH:1]([C:3]1[CH:12]=[C:11]([CH:13]([CH3:15])[CH3:14])[C:10]2[C:5](=[C:6]([CH3:17])[CH:7]=[CH:8][C:9]=2[CH3:16])[N:4]=1)[NH2:2].[Cl:18][C:19]1[CH:20]=[C:21]([N:26]=[C:27]=[O:28])[CH:22]=[C:23]([Cl:25])[CH:24]=1>>[Cl:18][C:19]1[CH:20]=[C:21]([NH:26][C:27]([NH:2][NH:1][C:3]2[CH:12]=[C:11]([CH:13]([CH3:14])[CH3:15])[C:10]3[C:5](=[C:6]([CH3:17])[CH:7]=[CH:8][C:9]=3[CH3:16])[N:4]=2)=[O:28])[CH:22]=[C:23]([Cl:25])[CH:24]=1

Participants

3

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 670830992-Hydrazinyl-4-isopropyl-5,8-dimethylquinoline

Product 1

HCID 52912058N-(3,5-Dichlorophenyl)-2-(4-isopropyl-5,8-dimethylquinolin-2-yl)hydrazinecarboxamide

Procedure

A solution of 2-hydrazinyl-4-isopropyl-5,8-dimethylquinoline (100 mg, 0.44 mmol) and 82 mg (1.0 eq) of 3,5-dichlorophenyl isocyanate was reacted as outlined in Scheme 1 above to give the desired title compound. Spectroscopic data: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.23 (d, J=6.74 Hz, 6 H) 2.42 (s, 3 H) 2.74 (s, 3 H) 3.88-4.06 (m, 1 H) 6.89 (s, 1 H) 6.94 (d, J=7.33 Hz, 1 H) 7.07 (t, J=1.90 Hz, 1 H) 7.22 (d, J=7.03 Hz, 1 H) 7.65 (br. s., 2 H) 8.27 (br. s., 1 H) 8.58 (s, 1 H) 9.24 (br. s., 1 H).

Sources & evidence

ORD record
ord-9b633b9f270d4927a8be466a7328343b
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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