Hydrazine hydrate (1:1) → HCID 68183388, compound

HRID 513587Notes

Reaction equation

HRID 513587 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=1[N+:26]([O-])=O)(=[O:15])=[O:14].O.NN>[Ni]>[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:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([CH3:1])=[CH:11]2)(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68183005HCID 68183005, compound2×

Product 1

HCID 68183388HCID 68183388, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In a similar fashion using route 6 general procedure 14, N-(3-Methylquinolin-8-yl)-2-nitro-4-trifluoromethylbenzenesulfonamide (Intermediate 158) (60 mg, 0.14 mmol), Raney nickel (10 mg, 20% wt) and hydrazine hydrate (20 mg, 0.43 mmol) gave the title compound (12 mg, 22%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-bf0e7c9bb266489aa7f100e42f2e9055
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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