HCID 12888773, compound → HCID 135759095, compound
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]#[N:8])[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[N+:17]([O-])=O)=[N:3]1>C(O)C.Cl>[NH2:8][C:7]1[C:5]2[C:4](=[N:3][N:2]([CH3:1])[CH:6]=2)[NH:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[N:17]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To 1-methyl-3-(4-chloro-2-nitroanilino)pyrazole-4-carbonitrile (16 g) stirred in ethanol (500 ml) was added a solution of anhydrous stannous chloride (33.1 g) in concentrated hydrochloric acid (176 ml). The mixture was heated under reflux for 2 hours, cooled, filtered and crystallised from methylated spirits (1 liter) to give the title compound as its hydrochloride salt m.p.>260° C. 2.0 g of the hydrochloride salt was partitioned between dilute ammonia solution and chloroform. The organic phase was washed with water, dried with magnesium sulphate, evaporated and the residue crystallised from chloroform-n-hexane to give the title compound as the free base m.p. 240° C.