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

HRID 2292913Notes

Reaction equation

HRID 2292913 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 dihydrate (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-1ea00a0571ef4050a0b02ed79be11a88
Source dataset
uspto-grants-1997_11
Patent number
US05684198

Reaction notes

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