3-chloro-N-(2-hydroxyphenyl)propanamide → 8-Hydroxy-3,4-dihydroquinolin-2(1h)-one

HRID 456401Notes

Reaction equation

HRID 456401 reaction equation
Cl[CH2:2][CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>>[OH:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[NH:6][C:4](=[O:5])[CH2:3][CH2:2]2

Participants

3

Reactant 2

HCID 34055143-chloro-N-(2-hydroxyphenyl)propanamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2682398-Hydroxy-3,4-dihydroquinolin-2(1h)-oneYield 46.6%

Procedure

A mixture of 3-chloro-N-(2-hydroxyphenyl)propanamide (0.25 g, 1.25 mmol) and aluminium chloride (AlCl3) (0.5 g) was heated with stirring at 130–135° C. for 5 h. After cooling to room temperature, the reaction mixture was quenched with water (3 ml), and extracted with ethyl acetate (3×5 ml). Evaporation of the solvent and flash chromatography of the residue on silica gel with ethyl acetate/heptane (1:1) afforded colourless crystals of the subtitled compound (95 mg, 46.5%).

Workup

  1. temperaturewas heated
  2. customthe reaction mixture was quenched with water (3 ml)
  3. extractionextracted with ethyl acetate (3×5 ml)
  4. customEvaporation of the solvent and flash chromatography of the residue on silica gel with ethyl acetate/heptane (1:1)

Sources & evidence

ORD record
ord-b56ba56d039c4bd1b9fab96310f1e22a
Source dataset
uspto-grants-2007_03
Patent number
US07186718B2

Reaction notes

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