N-(6-methoxy-5-methylpyridin-3-yl)-2-nitrobenzenesulfonamide → 2-amino-N-(6-methoxy-5-methylpyridin-3-yl)benzenesulfonamide

HRID 1772879Notes

Reaction equation

HRID 1772879 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)(=[O:12])=[O:11])=[CH:5][C:4]=1[CH3:22]>[Pd].C(O)C.CCOC(C)=O>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([NH:9][C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[C:4]([CH3:22])[CH:5]=1)(=[O:11])=[O:12]

Participants

4

Reactant 1

HCID 90022532N-(6-methoxy-5-methylpyridin-3-yl)-2-nitrobenzenesulfonamide

Product 1

HCID 900307172-amino-N-(6-methoxy-5-methylpyridin-3-yl)benzenesulfonamideYield 106.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of N-(6-methoxy-5-methylpyridin-3-yl)-2-nitrobenzenesulfonamide (2.69 g, 8.32 mmol) and 10% palladium on charcoal (1.35 g) in ethanol/EtOAc (1:1, 100 mL total reaction volume) was stirred at rt under an atmosphere of H2 for approximately 2.5 h. Filtration and concentration in vacuo yielded the crude title compound (2.60 g).

Workup

  1. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-886338baa49241c6a370f08fa640ef18
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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