HCID 351251, compound → 4-(3-Pyridinylsulfonyl)benzenamine

HRID 327167Notes

Reaction equation

HRID 327167 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=1.C(=O)(O)[O-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=1

Participants

4

Reactant 2

HCID 351251HCID 351251, compoundHCID 516892Sodium Bicarbonate

Product 1

HCID 107283864-(3-Pyridinylsulfonyl)benzenamineYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-nitrophenyl 3-pyridyl sulfone (1.60 g, 6.1 mmol) and stannous chloride dehydrate (6.83 g, 30.2 mmol) in absolute ethanol (20 mL) was heated at reflux for 45 min. The reaction mixture was poured into ice water, and the aqueous solution basified with sodium bicarbonate (pH=8-9) and extracted with ethyl acetate (2×200 mL). The organics were combined, dried (MgSO4), filtered, and the solvent distilled to yield the title benzenamine (1.10 g, 79%) as a pale yellow solid; mp 182°-184° C. 1H--NMR (300 MHz, d6 --DMSO): 6.29 (broad s, 2H, NH2), 6.64 (d, 2H, J=11.2 Hz, aromatic), 7.58 (m, 1H, aromatic), 7.61 (d, 2H, J=11.1 Hz, aromatic), 8.21 (dd, 1H, J=9.8, 2.4 Hz, aromatic), 8.78 (dd, 1H, J=9.9, 1.4 Hz, aromatic), 9.01 (d, 1H, J=2.4 Hz). MS (CI, CH4): 235(M+1).

Workup

  1. temperatureat reflux for 45 min
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. distillationthe solvent distilled

Sources & evidence

ORD record
ord-6c405a67a49d4e569d3d0f9aa9f5e3b5
Source dataset
uspto-grants-1993_12
Patent number
US05272163

Reaction notes

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