gamma-Octalactone → 4-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 2118696노트

반응식

HRID 2118696 반응식
[C:1]1([NH:7][C:8]2[N:17]=[CH:16][CH:15]=[CH:14][C:9]=2[C:10]([O:12]C)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][CH2:19][CH2:20][CH2:21][CH:22]1[O:27][C:25](=[O:26])[CH2:24][CH2:23]1.CC(C)([O-])C.[K+]>[OH-].[Na+]>[OH:12][C:10]1[C:9]2[C:8](=[N:17][CH:16]=[CH:15][CH:14]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:25](=[O:26])[C:24]=1[CH2:23][CH:22]([OH:27])[CH2:21][CH2:20][CH2:19][CH3:18]

참가 물질

5

반응물 3

HCID 7704gamma-OctalactoneHCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 547178204-hydroxy-3-(2-hydroxyhexyl)-1-phenyl-1,8-naphthyridin-2(1H)-one

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

반응 조건

온도
95 °C

실험 절차

A mixture of methyl 2-phenylaminonicotinate (5 g.), gamma-octanoic lactone (10 g.) and potassium t-butoxide (7.5 g.) was stirred in a nitrogen atmosphere and heated to 95° C. where it was held for 6 hrs. After cooling, the mixture was poured into 5% NaOH (200 ml.) and stirred overnight. Acidification to pH 4.6 yielded an oil, which was extracted with ether, washed with water, dried (Na2SO4), filtered, and evaporated to a small volume. Hexane was added until turbidity was noticed, and the mixture was allowed to stand for about 5 hrs. The solid was filtered off and recrystallized from CH2Cl2 /isopropanol/isopropyl ether to produce the desired product, m.p. 184°-186° C.

후처리

  1. temperatureAfter cooling
  2. stirringstirred overnight
  3. customAcidification to pH 4.6 yielded an oil, which
  4. extractionwas extracted with ether
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated to a small volume
  9. additionHexane was added until turbidity
  10. waitto stand for about 5 hrs
  11. filtrationThe solid was filtered off
  12. customrecrystallized from CH2Cl2 /isopropanol/isopropyl ether

출처 및 근거

ORD 기록
ord-7a1479383b654134af544427cd1903a4
출처 데이터셋
uspto-grants-1987_07
특허 번호
US04680297

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