Sodium Hydroxide → 2,3-dihydroquinolin-4(1H)-one

HRID 1097781Notes

Reaction equation

HRID 1097781 reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>[NH:7]1[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:10](=[O:12])[CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 244082N-Phenyl-beta-alanine

Product 1

HCID 1171582,3-dihydroquinolin-4(1H)-oneYield 46.3%

Reagents, catalysts & solvents 1

HCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidSolvent

Conditions

Temperature
70 °C

Procedure

The mixture of 3-phenylamino-propionic acid (1.22 g, 7.39 mmol) in Eaton's reagent (40 mL) is stirred at 70° C. for overnight. The resulting mixture is poured into ice and basified by the slow addition of NaOH (50%) solution. The basified mixture is extracted with ethyl acetate and washed by brine, and dried over anhydrous sodium sulfate. After concentration, the residue is purified by flash chromatography, and gives the title compound (0.5 g, 46.3% yield).

Workup

  1. additionThe resulting mixture is poured into ice
  2. extractionThe basified mixture is extracted with ethyl acetate
  3. washwashed by brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-4ad7170f40ae46cdb1b66995c9c5e5b6
Source dataset
uspto-grants-2012_03
Patent number
US08143278B2

Reaction notes

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