Sodium Bicarbonate → 4-(2-Pyridylsulfonyl)aniline

HRID 2292915Notes

Reaction equation

HRID 2292915 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)(=[O:9])=[O:8].C(=O)(O)[O-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7]([C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 214801062-(4-Nitrobenzene-1-sulfonyl)pyridine

Product 1

HCID 105138504-(2-Pyridylsulfonyl)anilineYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-nitrophenyl 2-pyridyl sulfone (6.50 g, 24.6 mmol) and stannous chloride dihydrate (27.72 g, 123.0 mmol) in absolute ethanol (200 mL) was heated at reflux for 25 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 (2×400 mL). The organics were combined, dried (MgSO4), filtered, and the solvent distilled to yield the title benzenamine (5.12 g, 89%) as a white solid; mp 158°-160° C. 1H-NMR (300 MHz, d6 -DMSO): 6.27 (broad s, 2H, NH2), 6.66 (d, 2H, J=8.7 Hz, aromatic), 7.61 (m, 3H, aromatic), 8.08 (d, 2H, J=4.9 Hz, aromatic), 8.68 (d, 1H, J=4.9, aromatic). MS (CI, CH4): 235(M+1).

Workup

  1. temperatureat reflux for 25 min
  2. extractionextracted with ethyl acetate (2×400 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. distillationthe solvent distilled

Sources & evidence

ORD record
ord-94faf520939d4a12a25e168909c9b5ca
Source dataset
uspto-grants-1997_11
Patent number
US05684198

Reaction notes

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