Ethyl benzoylacetate → 4-Hydroxy-6-methyl-2-phenylquinoline

HRID 572149Notes

Reaction equation

HRID 572149 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]([CH2:17][C:18](OCC)=[O:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[Na+]>>[CH3:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[NH:1][C:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH:17][C:18]2=[O:19]

Participants

4

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 7813p-ToluidineHCID 14798Sodium Hydroxide

Product 1

HCID 7308104-Hydroxy-6-methyl-2-phenylquinoline

Conditions

Temperature
130 °C

Procedure

A mixture of p-toluidine (2.14 g, 0.02 mole), ethyl benzoylacetate (4.9 g, 0.025 mole), and polyphosphoric acid (PPA) was heated at 130° C. with stirring. After the reaction was complete, the mixture was cooled to room temperature and neutralized with 4 M NaOH. The yellow solid was filtered, washed with water, dried and recrystallized from ethanol to give compound I-8-a as white solid (2.9 g, 48.9%).

Workup

  1. filtrationThe yellow solid was filtered
  2. washwashed with water
  3. customdried
  4. customrecrystallized from ethanol
  5. customto give compound

Sources & evidence

ORD record
ord-9685c1fa9013444d8fc5a4bf6fed3203
Source dataset
uspto-grants-2015_05
Patent number
US09029394B2

Reaction notes

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