Pyridine → Pyridine-2-sulfonic acid (4-formyl-phenyl)-amide

HRID 970938Notes

Reaction equation

HRID 970938 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])=[CH:5][CH:4]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(=[O:12])=[O:11])=[CH:7][CH:8]=1)=[O:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 85814308Pyridine-2-sulfonic acid (4-hydroxymethyl-phenyl)-amide

Product 1

HCID 85814309Pyridine-2-sulfonic acid (4-formyl-phenyl)-amideYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of pyridine-2-sulfonic acid (4-hydroxymethyl-phenyl)-amide (200 mg, 0.76 mmol), and pyridine (612 uL) in anhydrous CH2Cl2 (3 mL) was added Dess-Martin periodiane (450 mg, 1.06 mmol). The resultant solution was stirred at room temperature for 1 h. The mixture was diluted with 100 mL CH2Cl2, filtered through celite, and concentrated. The crude material was purified by recrystallisation from cold CH2Cl2 to give the title compound (120 mg, 60%) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 7.34 (d, 2H, J=8.4 Hz), 7.49-7.50 (m, 1H), 7.74 (br s, 1H), 7.75 (d, 2H, J=8.4 Hz), 7.89-7.70 (m, 1H), 8.03 (d, 1H, J=8.1 Hz), 8.70 (d, 1H, J=4.2 Hz), 9.87 (s, 1H).

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated
  3. customThe crude material was purified by recrystallisation from cold CH2Cl2

Sources & evidence

ORD record
ord-330186af845847758b64f7fceddc184e
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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