Hydrazine hydrate (1:1) → 2-Amino-N-(5-chloroquinolin-8-yl)-4-methyl-benzenesulfonamide

HRID 513584Notes

Reaction equation

HRID 513584 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[N+:23]([O-])=O)(=[O:15])=[O:14])=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.O.NN>[Ni].CO>[NH2:23][C:17]1[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=1[S:13]([NH:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]2[C:8]=1[N:7]=[CH:6][CH:5]=[CH:4]2)(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68183028N-(5-chloroquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamide2×

Product 1

HCID 681833692-Amino-N-(5-chloroquinolin-8-yl)-4-methyl-benzenesulfonamideYield 27.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a similar fashion using route 6 general procedure 14, N-(5-chloroquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamide (Intermediate 155) (160 mg, 0.42 mmol), Raney nickel (32 mg, 20% wt), hydrazine hydrate (63 mg, 1.27 mmol) and MeOH (10 ml) gave the title compound (40 mg, 27%) after purification by column chromatography with DCM as the eluent followed by recrystallisation from DCM/n-pentane.

Sources & evidence

ORD record
ord-b20cd9743a174eae814829f53ca41788
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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