Diethyl (ethoxymethylene)malonate → Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate

HRID 1070646

反応式

HRID 1070646 の反応式
[CH3:1][C:2]1[C:7]([NH2:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>C1(C)C(C)=CC=CC=1>[OH:12][C:13]1[C:6]2[C:7](=[C:2]([CH3:1])[N:3]=[C:4]([CH3:9])[CH:5]=2)[N:8]=[CH:20][C:14]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

参加物

4

反応物 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 769642,6-Dimethyl-3-pyridylamine

生成物 1

HCID 22397159Ethyl 4-Hydroxy-6,8-dimethyl-1,7-naphthyridine-3-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

A mixture of 2,6-dimethyl-3-aminopyridine (0.85 g) and diethyl ethoxymethylenemalonate (1.53 g) is heated at 135° C. in xylene (30 mL) for 2 h allowing for removal of ethanol. After the solvent is removed, the mixture is suspended in diphenyl ether (15 mL). The mixture is then heated to reflux with removal of ethanol for 30 min. The reaction mixture is cooled to room temperature and hexanes (20 mL) is added. The resulting precipitate is filtered, washed with diethyl ether (2×10 mL) and dried to give 0.5 g (30%) of the title compound as a brown solid. Physical chracteristics: MS (ESI+) m/z 247 (M+H)+; 1H NMR (DMSO) δ8.67, 7.97, 4.38, 2.85, 2.67, 1.40.

後処理

  1. customallowing for removal of ethanol
  2. customAfter the solvent is removed
  3. temperatureThe mixture is then heated
  4. temperatureto reflux with removal of ethanol for 30 min
  5. additionhexanes (20 mL) is added
  6. filtrationThe resulting precipitate is filtered
  7. washwashed with diethyl ether (2×10 mL)
  8. customdried

出典と根拠

ORDレコード
ord-5a6afead07e946eebdff6669cdb69237
出典データセット
uspto-grants-2005_06
特許番号
US06903097B2

関連ノート

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