Hydrazine hydrate (1:1) → 2-Amino-N-(6-methoxy-quinolin-8-yl)-4-methyl-benzenesulfonamide

HRID 513582Notes

Reaction equation

HRID 513582 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=3[N+:24]([O-])=O)(=[O:16])=[O:15])[CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.O.NN>[Ni]>[NH2:24][C:18]1[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=1[S:14]([NH:13][C:11]1[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=[C:5]2[C:10]=1[N:9]=[CH:8][CH:7]=[CH:6]2)(=[O:15])=[O:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 16759965N-(6-methoxyquinolin-8-yl)-4-methyl-2-nitrobenzenesulfonamide2×

Product 1

HCID 167599112-Amino-N-(6-methoxy-quinolin-8-yl)-4-methyl-benzenesulfonamideYield 44%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

In a similar fashion using route 6 general procedure 14, N-(6-methoxyquinolin-8-yl)-4-methyl-2-nitro-benzenesulfonamide (Intermediate 153) (150 mg, 0.40 mmol), Raney nickel (30 mg, 20% wt) and hydrazine hydrate (64 mg, 1.21 mmol) gave title compound (60 mg, 44%) after purification by column chromatography with DCM as the eluent.

Sources & evidence

ORD record
ord-dbc0737d9ec64d7589b919d28d976ca0
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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