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

HRID 1658103

반응식

HRID 1658103 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-f7977644778c4d61b860733ae2aeb384
출처 데이터셋
uspto-grants-1976_06
특허 번호
US03962445

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