HCID 14538888, compound → 4-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridine

HRID 964128Notes

Reaction equation

HRID 964128 reaction equation
[C:1]1(=[O:22])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[Na].[BH4-]>C(O)C>[OH:22][CH:1]1[C:2]2[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4](=[O:17])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14538888HCID 14538888, compoundHCID 131720715CID 131720715

Product 1

HCID 190790764-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridineYield 27.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.25 g (20.0 mol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium-borohydride was added, and the mixture was stirred at room temperature for 2.5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 1.73 g of the desired compound (27.5% yield, colorless crystals), mp. 144°-145° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-9cbeacfe7a1f4ba1bacf020de488c035
Source dataset
uspto-grants-1998_06
Patent number
US05767121

Reaction notes

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