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

HRID 513585Notes

Reaction equation

HRID 513585 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]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[N+:26]([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>[NH2:26][C:17]1[CH:18]=[C:19]([C:22]([F:24])([F:23])[F:25])[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:14])=[O:15]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68182997N-(5-Chloroquinolin-8-yl)-2-nitro-4-trifluoromethylbenzenesulfonamide2×

Product 1

HCID 681830122-Amino-N-(5-chloroquinolin-8-yl)-4-trifluoromethyl-benzenesulfonamideYield 27%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In the similar fashion using route 6 general procedure 14, N-(5-chloroquinolin-8-yl)-2-nitro-4-trifluoromethylbenzenesulfonamide (Intermediate 156) (120 mg, 0.28 mmol), Raney nickel (24 mg, 20% wt), hydrazine hydrate (40 μl, 0.84 mmol), MeOH (3 ml) gave the title compound (30 mg, 27%) after purification by column chromatography with DCM/MeOH (199:1) as the eluent.

Sources & evidence

ORD record
ord-917204f6d7444dff935aa1ec7f7f86c6
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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