N-Phenylanthranilic Acid → 4-Hydroxy-1-phenyl-1,2-dihydroquinolin-2-one

HRID 462072

Reaction equation

HRID 462072 reaction equation
[C:1]1([NH:7][C:8]2[C:9](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:10]([OH:12])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](OC(=O)C)(=[O:19])[CH3:18].[OH-].[Na+]>C(O)(=O)C>[OH:12][C:10]1[C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:17](=[O:19])[CH:18]=1

Participants

5

Reactant 3

HCID 4386N-Phenylanthranilic AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide

Product 1

HCID 546761614-Hydroxy-1-phenyl-1,2-dihydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of N-phenyl anthranilic acid (30.1g.; 0.146 mole) and acetic anhydride (74 ml.) in glacial acetic acid (74 ml.) was refluxed for 4 hrs. The resulting red solution was cooled, poured onto crushed ice-water (600 ml) and brought to pH 9 with dilute sodium hydroxide solution. After filtration the clear liquid was taken to pH 5 with hydrochloric acid and the white solid filtered off and dried, m.p. (AcOH) 298°-300° C. (Found: C, 75.40; H, 4.58; N, 5.70; C15H11NO2 requires; C, 75.94; H, 4.67; N, 5.90%).

Workup

  1. temperatureThe resulting red solution was cooled
  2. additionpoured
  3. filtrationAfter filtration the clear liquid
  4. filtrationthe white solid filtered off
  5. customdried
  6. customm.p. (AcOH) 298°-300° C. (Found: C, 75.40; H, 4.58; N, 5.70; C15H11NO2 requires; C, 75.94; H, 4.67; N, 5.90%)

Sources & evidence

ORD record
ord-f96771a0959d4d0d85fe7f03f62fc23e
Source dataset
uspto-grants-1977_12
Patent number
US04065457

Linked notes

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