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

HRID 2097054ノート

反応式

HRID 2097054 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-ad9384e23fc5401bbe64bbcfd60d6920
出典データセット
uspto-grants-2013_05
特許番号
US08450307B2

反応ノート

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