Tetrahydrofuran → 3-Amino-N-pyridin-3-ylmethyl-benzenesulfonamide

HRID 2224395Notes

Reaction equation

HRID 2224395 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C1COCC1>CO>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:13][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 2887009HCID 2887009, compound

Product 1

HCID 31976503-Amino-N-pyridin-3-ylmethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrogenation of a stirred solution of 3-nitro-N-pyridin-3-ylmethyl-benzenesulfonamide [CAS-No. 436095-43-1; commercially available] (1.42 g, 4.84 mmol) in methanol (90 ml) and THF (50 ml) on palladium/carbon (10%, 0.14 g) for 2 h at room temperature yielded after removal of the catalyst by filtration, evaporation and crystallization from ethyl acetate/hexane the title compound (1.15 g, 90%) as a light yellow solid. MS (ISP) 264.1 [(M+H)+]; mp 129° C.

Workup

  1. customafter removal of the catalyst
  2. filtrationby filtration, evaporation and crystallization from ethyl acetate/hexane the title compound (1.15 g, 90%) as a light yellow solid

Sources & evidence

ORD record
ord-e3d900a1711347f0b3739e05f36b3cc0
Source dataset
uspto-grants-2008_05
Patent number
US07378417B2

Reaction notes

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