Acetic Acid → 1-Ethyl-4-hydroxyquinolin-2(1H)-one

HRID 462062Notes

Reaction equation

HRID 462062 reaction equation
[CH2:1]([NH:3][C:4]1[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:6](O)=[O:7])[CH3:2].[OH-:13].[Na+].[C:15](O)(=O)[CH3:16]>C(OC(=O)C)(=O)C>[CH2:15]([N:3]1[C:4]2[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6]([OH:7])=[CH:2][C:1]1=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 66642Benzoic acid, 2-(ethylamino)-

Product 1

HCID 546846411-Ethyl-4-hydroxyquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of N-ethyl anthranilic acid (12.0g; 0.073 mole) in acetic acid (37 ml) and acetic anhydride (37ml) was refluxed for 4 hrs. The red solution was cooled, poured onto crushed ice and made alkaline with aqueous sodium hydroxide. After filtering the yellow filtrate was neutralised with concentrated hydrochloric acid (pH 5) and the yellow solid filtered and washed with water. Recrystallisation from acetic acid in the presence of charcoal gave the title compound as an orange solid, m.p. 273°-275° C. (Found: C, 69.85; H, 6.04; N, 7.29; C11H11NO2 requires: C, 69.83; H, 5.86; N, 7.40%).

Workup

  1. temperatureThe red solution was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationAfter filtering the yellow filtrate
  5. filtrationthe yellow solid filtered
  6. washwashed with water
  7. customRecrystallisation from acetic acid in the presence of charcoal

Sources & evidence

ORD record
ord-0d5f63e3f93643dd86adb8cbf835feb7
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Reaction notes

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