Hydrazine hydrate (1:1) → HCID 68182972, compound

HRID 513586Notes

Reaction equation

HRID 513586 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[N:20]=[CH:19][C:18]([CH3:22])=[CH:17]3)(=[O:10])=[O:9])=[C:4]([N+:23]([O-])=O)[CH:3]=1.O.NN>[Ni].CO.C1COCC1>[NH2:23][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][C:18]([CH3:22])=[CH:17]2)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68183269HCID 68183269, compound2×

Product 1

HCID 68182972HCID 68182972, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

In a similar fashion using route 6 general procedure 14, 4-methyl-N-(3-methylquinolin-8-yl)-2-nitrobenzenesulfonamide (Intermediate 157) (100 mg, 0.28 mmol), Raney nickel (20 mg, 20% wt), hydrazine hydrate (42 mg, 0.84 mmol) and MeOH/THF (4:1, 5 ml) gave the title compound (20 mg, 22%) after purification by column chromatography with n-hexane/EtOAc (1:0-4:1) gradient elution.

Sources & evidence

ORD record
ord-8a0d6794ee0c4e5a959c38c728dd49d9
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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