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Diethyl 2-(((6-methoxypyridin-3-yl)amino)methylene)malonate → Ethyl 4-hydroxy-6-methoxy-1,5-naphthyridine-3-carboxylate

HRID 734209
ノート
印刷プレビュー

反応式

HRID 734209 の反応式
C(O[C:4](=[O:21])[C:5](=[CH:11][NH:12][C:13]1[CH:14]=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH2:9]([O:8][C:6]([C:5]1[C:4](=[O:21])[C:14]2[C:13](=[CH:18][CH:17]=[C:16]([O:19][CH3:20])[N:15]=2)[NH:12][CH:11]=1)=[O:7])[CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

3

反応物 1

HCID 619151Diethyl 2-(((6-methoxypyridin-3-yl)amino)methylene)malonate

生成物 1

HCID 600736Ethyl 4-hydroxy-6-methoxy-1,5-naphthyridine-3-carboxylate収率 73.1%

試薬・触媒・溶媒 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)溶媒

実験手順

Dowtherm A (Fluka, 500 mL) was brought to boiling (250° C.) in a 2 L 3-neck flask fitted with a still-head and a reflux condenser. 2-[(6-Methoxypyridin-3-ylamino)methylene]malonic acid diethyl ester (100 g, 0.34 mole) was added portionwise over 5 min. The solution was heated at reflux for an additional 15 min, allowing some solvent to distill over. The resulting solution was cooled to RT and diluted with hexanes (750 mL). The mixture was cooled in ice for 1 hr, then the brown solid was filtered off, washed with hexanes, and dried under vacuum to afford the title compound (61.72 g, 73%).

後処理

  1. custom(250° C.)
  2. customfitted with a still-head and a reflux condenser
  3. temperatureThe solution was heated
  4. temperatureat reflux for an additional 15 min
  5. distillationto distill over
  6. additiondiluted with hexanes (750 mL)
  7. temperatureThe mixture was cooled in ice for 1 hr
  8. filtrationthe brown solid was filtered off
  9. washwashed with hexanes
  10. customdried under vacuum

出典と根拠

ORDレコード
ord-787d7d86387e4b2c857b1fccc9e27117
出典データセット
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07592334B2

反応ノート

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