Diethyl Malonate → Ethyl 6-bromo-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1362308노트

반응식

HRID 1362308 반응식
[NH2:1][C:2]1[C:7]([CH:8]=O)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=1.[C:11](OCC)(=[O:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].N1CCCCC1>CCO>[CH2:16]([O:15][C:13]([C:12]1[C:11](=[O:18])[NH:1][C:2]2[C:7]([CH:8]=1)=[CH:6][C:5]([Br:10])=[CH:4][N:3]=2)=[O:14])[CH3:17]

참가 물질

5

반응물 3

HCID 7761Diethyl MalonateHCID 8082PiperidineHCID 242137922-Amino-5-bromo-3-pyridinecarbaldehyde

생성물 1

HCID 53396436Ethyl 6-bromo-2-oxo-1,2-dihydro-1,8-naphthyridine-3-carboxylate수율 57.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 2-amino-5-bromo-pyridine-3-carbaldehyde (4.00 g, 14.2 mmol), diethyl malonate (21.6 mL, 142 mmol) and piperidine (7.00 mL, 71.0 mmol) in EtOH (70 mL) was heated to reflux overnight. The mixture was cooled to room temperature and the solid was collected by filtration to give the title compound (2.41 g, 57%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 12.65 (s, 1H), 8.70 (d, J=2.4 Hz, 1H), 8.56 (d, J=2.4 Hz, 1H), 8.45 (s, 1H), 4.29 (q, J=7.1 Hz, 2H), 1.30 (t, J=7.1 Hz, 3H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. filtrationthe solid was collected by filtration

출처 및 근거

ORD 기록
ord-1e972c7186354cd485e2c54c55fe2396
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879872B2

반응 노트

불러오는 중…