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

HRID 42275Notes

Reaction equation

HRID 42275 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-cb5be109acf34a3dbe7b89528e30b867
Source dataset
uspto-grants-2013_09
Patent number
US08536181B2

Reaction notes

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