Hydrochloric Acid → 4-Hydroxy-1,3,3-trimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1097779Notes

Reaction equation

HRID 1097779 reaction equation
[BH4-].[Na+].[CH3:3][N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[C:6]([CH3:16])([CH3:15])[C:5]1=[O:17].Cl>CCO>[OH:14][CH:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:4]([CH3:3])[C:5](=[O:17])[C:6]1([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 992162,4-Quinolinedione, 1,2,3,4-tetrahydro-1,3,3-trimethyl-HCID 4311764Sodium borohydride

Product 1

HCID 1037624-Hydroxy-1,3,3-trimethyl-3,4-dihydroquinolin-2(1H)-oneYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

NaBH4 (excess amount) is added to a solution of 1,3,3-Trimethyl-1H-quinoline-2,4-dione (330 mg, 1.62 mmol) in EtOH (8 mL) at 0° C. The resulting mixture is slowly warmed up to room temperature. After 1 h, HCl (10%, 3 mL) is added dropwise. The solvent is removed under vacuum, the residue is dissolved into ether and washed with water, brine, and dried over anhydrous Na2SO4. After concentration, the title compound is yielded (275 mg, 82% yield).

Workup

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue is dissolved into ether
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-c63cda62eac443e8bccd8558c3f3c63a
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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