Water → 5-Nitro-2-(4-oxo-2-phenyl-3,4-dihydrobenzo[1.4]oxathiin-6-yloxy)pyridine

HRID 31317Notes

Reaction equation

HRID 31317 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:17][S:16][C:15]=3[CH:26]=2)=[N:8][CH:9]=1)([O-:3])=[O:2].[OH2:27]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]3[O:19][CH:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:17][S:16](=[O:27])[C:15]=3[CH:26]=2)=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 962WaterHCID 179786105-Nitro-2-(2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-yloxy)pyridine

Product 1

HCID 179786225-Nitro-2-(4-oxo-2-phenyl-3,4-dihydrobenzo[1.4]oxathiin-6-yloxy)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-nitro-2-(2-phenyl-2,3-dihydrobenzo[1,4]oxathiin-6-yloxy)pyridine (214 mg) in methanol (80 ml) at 60° C., NaIO4 (total 2.5 eq) was added in small portions until disappearance of the starting material. The mixture was poured into water and precipitate was filtered and washed with water. The crude product was purified by column chromatography using heptane-ethyl acetate (1:1) as an eluant. 1H NMR (400 MHz, CDCl3) δ: 9.02 (d, 1H, J 2.8 Hz), 8.51 (dd, 1H, J 9.1, 2.8 Hz), 7.45-7.56 (m, 6H), 7.32 (dd, 1H, J 9.0, 2.8 Hz), 7.21 (d, 1H, J 9.0 Hz), 7.10 (d, 1H, J 9.1 Hz), 5.77 (dd, 1H, J 12.0, 1.5 Hz), 3.34 (dd, 1H, 14.4, 1.5 Hz), 3.13 (dd, 1H, 14.4, 12.0 Hz).

Workup

  1. filtrationwas filtered
  2. washwashed with water
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-7ac67ebb485c4528839a51aaea0ea851
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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