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

HRID 487389노트

반응식

HRID 487389 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH2:10][CH3:11])[C:3]=1[CH:12]=[O:13].C([C:16](CC)([C:20]([O-:22])=O)[C:17]([O-:19])=[O:18])C.[CH2:25](O)[CH3:26]>N1CCCCC1>[CH2:10]([C:4]1[N:5]=[C:6]([CH2:8][CH3:9])[CH:7]=[C:2]2[C:3]=1[C:12]([OH:13])=[C:16]([C:17]([O:19][CH2:25][CH3:26])=[O:18])[C:20](=[O:22])[NH:1]2)[CH3:11]

참가 물질

5

반응물 3

HCID 702EthanolHCID 69515632,2-DiethylpropanedioateHCID 190937814-Amino-2,6-diethyl-pyridine-3-carbaldehyde

생성물 1

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

시약·촉매·용매 1

HCID 8082Piperidine촉매

실험 절차

4-amino-2,6-diethylpyridine-3-carbaldehyde (1.78 g), diethylmalonate (1.92 g), ethanol (15 ml) and piperidine (4 drops) were heated at reflux for 16 hours. Volatile material was removed by evaporation and the residue was recrystallised from ethyl acetate/petroleum ether to give ethyl 5,7-diethyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxylate (B) (1.4 g), m.p. 159°-160° C.; NMR (CDCl3): 1.34(t, 3H), 1.38(t, 3H), 1.47(t, 3H), 2.87(q, 2H), 3.14(q, 2H), 4.47(q, 2H), 7.03(s, 1H), 8.78(s, 1H), 12.2(s, 1H); mass spectrum (CI, ammonia): 275 (M+H)+ ; microanalysis, found: C, 65.8; H, 6.8; N, 10.4%; C15H18N2O3 requires: C, 65.7; H, 6.6; N, 10.2%.

후처리

  1. temperatureat reflux for 16 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was recrystallised from ethyl acetate/petroleum ether

출처 및 근거

ORD 기록
ord-9c17c46f14f949cd908330fb5aa817d4
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05294620

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