Hydrochloric Acid → 1-(4-chlorobenzyl)-3-hydroxypyridin-2(1H)-one

HRID 1875308Notes

Reaction equation

HRID 1875308 reaction equation
[Si]([O:8][C:9]1[C:10](=[O:23])[N:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18](Cl)[CH:17]=2)[CH:12]=[CH:13][CH:14]=1)(C(C)(C)C)(C)C.[ClH:24]>CCOC(C)=O>[Cl:24][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:11]2[CH:12]=[CH:13][CH:14]=[C:9]([OH:8])[C:10]2=[O:23])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67155133HCID 67155133, compound

Product 1

HCID 529122191-(4-chlorobenzyl)-3-hydroxypyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(tert-butyldimethylsilanyloxy)-1-(3-chlorobenzyl)-1H-pyridin-2-one, 2, (2.36 g, 10 mmol) in EtOAc (25 mL) as added 5 M HCl (25 mL) with vigorous stirring at room temperature. The reaction was monitored by TLC for the disappearance of starting material and was complete within 30 minutes. The organic layer was decanted and the aqueous phase extracted with dichloromethane (2×50 mL). The combined organic layers were dried over Na2SO4 and the solvent removed under reduced pressure. The crude product was recrystallized from dichloromethane. The yield was nearly quantitative. 1H NMR (360 MHz, DMSO-d6) δ ppm 5.12 (2H, s); 6.13 (1H, t, J=7.04); 6.71 (1H, dd, J=7.04, 1.59); 7.23-7.28 (2H, m); 7.36-7.43 (2H, m); 9.10 (1H, br. s).

Workup

  1. customThe organic layer was decanted
  2. extractionthe aqueous phase extracted with dichloromethane (2×50 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent removed under reduced pressure
  5. customThe crude product was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-654193c9d1eb40a784a0ab3d79f96c56
Source dataset
uspto-grants-2012_11
Patent number
US08309537B2

Reaction notes

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