Pyridine → HCID 136334156, compound

HRID 1372151Notes

Reaction equation

HRID 1372151 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:17]=O)=[C:12]3[C:16]=2[S:15][CH:14]=[CH:13]3)=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21].N1C=CC=CC=1>CO.CCOCC>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH:17]=[N:20][OH:21])=[C:12]3[C:16]=2[S:15][CH:14]=[CH:13]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 58779365HCID 58779365, compound

Product 1

HCID 136334156HCID 136334156, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a 10 ml round bottom flask was added 7-(4-hydroxyphenyl)-1-benzothiophene-4-carbaldehyde (61.7 mg, 0.24 mmol), hydroxylamine hydrochloride (34 mg, 0.49 mmol), and anhydrous pyridine (0.04 ml, 0.49 mmol) in MeOH (1.5 ml) was heated to reflux for 1 h and then allowed to cool. The mixture was then diluted with ether, washed with water and the organic layer was dried over anhydrous Na2SO4 then passed through a silica plug. Concentration under reduced pressure produced 60 mg of a slightly yellow solid and purification by column chromatography (40% EtOAc-hexanes) afforded 50 mg (92%) product as a slightly yellow solid: mp 230–231° C.; 1H NMR (300 MHz, DMSO-d6): δ 6.93 (2H, d, J=8.55 Hz), 7.38 (1H, d, J=7.63), 7.57 (2H, d, J=8.53 Hz), 7.68 (1H, d, J=7.71 Hz), 7.91 (1H, d, J=5.61 Hz), 8.12 (1H, d, J=5.64 Hz), 8.57 (1H, s), 9.77 (1H, s), 11.41 (1H, s); MS (ESI) m/z 270 ([M+H]+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 h
  3. temperatureto cool
  4. washwashed with water
  5. dry with materialthe organic layer was dried over anhydrous Na2SO4
  6. concentrationConcentration under reduced pressure
  7. customproduced
  8. custom60 mg of a slightly yellow solid and purification by column chromatography (40% EtOAc-hexanes)

Sources & evidence

ORD record
ord-99bb56abfd3641fb92eb989d4c1c5f84
Source dataset
uspto-grants-2007_01
Patent number
US07157491B2

Reaction notes

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