Diethyl Malonate → Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

HRID 1587502노트

반응식

HRID 1587502 반응식
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5]CC)=O.[NH2:12][C:13]1[CH:18]=[C:17]([CH2:19][CH3:20])[N:16]=[C:15]([CH2:21][CH3:22])[C:14]=1[C:23](OC)=[O:24].[Na]>C(O)C>[CH2:21]([C:15]1[N:16]=[C:17]([CH2:19][CH3:20])[CH:18]=[C:13]2[C:14]=1[C:23]([OH:24])=[C:2]([C:1]([O:9][CH2:10][CH3:11])=[O:8])[C:3](=[O:5])[NH:12]2)[CH3:22]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 20094263Methyl 4-amino-2,6-diethylpyridine-3-carboxylate

생성물 1

HCID 54684680Ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
150 °C

실험 절차

Diethyl malonate (14.5 ml) and methyl 4-amino-2,6-diethylpyridine-3-carboxylate (21.3 g) was added to a solution of sodium (2.33 g) in ethanol (60 ml) and the resulting mixture was heated at 150° C. for 20 hours in an autoclave. The mixture was allowed to cool and then volatile material was removed by evaporation and the resultant semi-crystalline solid was triturated with ether. The solid was collected by filtration and dissolved in a minimum of water. The solution as acidified with 2M hydrochloric acid and the resulting precipitate was collected by filtration and washed with water. The solid was dried under vacuum to give ethyl 5,7-diethyl-4-hydroxy-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate (B) (12.72 g); m.p. 240-242° C.; NMR (CDCl3): 1.34(dt, 6H), 1.52(t, 3H), 2.84(q, 2H), 3.36(q, 2H), 4.52(q, 2H), 6.87(s, 1H), 7.26(s, 1H), 11.41(broad, 1H); mass spectrum (CI, ammonia): 291 (M+H)+ ; microanalysis, found: C, 62.1; H, 6.2; N, 9.7%; C15H18N2O4 requires: C, 62.1; H, 6.3; N, 9.7%.

후처리

  1. temperatureto cool
  2. customvolatile material was removed by evaporation
  3. customthe resultant semi-crystalline solid was triturated with ether
  4. filtrationThe solid was collected by filtration
  5. dissolutiondissolved in a minimum of water
  6. filtrationthe resulting precipitate was collected by filtration
  7. washwashed with water
  8. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-ce9f4a271a794a70a5fa482dad255021
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05217976

반응 노트

불러오는 중…