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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
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HRID 734209 반응식
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]
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참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-787d7d86387e4b2c857b1fccc9e27117
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07592334B2

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