Dimethylformamide → 4-(1H-1,2,4-triazole-1-yl)-2-methyl-6-methoxy-quinoline

HRID 1030101Notes

Reaction equation

HRID 1030101 reaction equation
Cl.[CH3:2][C:3]1[CH:12]=[C:11](Cl)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[CH:9]=2)[N:4]=1.[NH:16]1[CH:20]=[N:19][CH:18]=[N:17]1.CN(C)C=O.[OH-].[NH4+]>O>[N:16]1([C:11]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([O:14][CH3:15])[CH:9]=3)[N:4]=[C:3]([CH3:2])[CH:12]=2)[CH:20]=[N:19][CH:18]=[N:17]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 14923Ammonium HydroxideHCID 198221334-Chloro-6-methoxy-2-methylquinoline hydrochloride

Product 1

HCID 148378264-(1H-1,2,4-triazole-1-yl)-2-methyl-6-methoxy-quinolineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.44 g of 2-methyl-4-chloro-6-methoxy-quinoline-hydrochloride, 1.38 g of 1,2,4-triazole and 10 ml of dimethyl formamide is stirred at 80° C. for 3 hours whereupon the reaction mixture is poured into 100 ml of water and neutralized with 2 ml of a concentrated ammonium hydroxide solution. The precipitated product is filtered. Thus 2.09 g of the desired compound are obtained, yield 87%, mp.: 117°-118° C.

Workup

  1. filtrationThe precipitated product is filtered

Sources & evidence

ORD record
ord-46b7782abfd1492db6b26c033b79e9fe
Source dataset
uspto-grants-1992_04
Patent number
US05104884

Reaction notes

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