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

HRID 1992253Notes

Reaction equation

HRID 1992253 reaction equation
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]

Participants

3

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 1

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

Procedure

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 portion-wise over 5 min. The solution was heated at reflux for an additional 15 min, allowing some solvent to distil over. The resulting solution was cooled to room temperature and diluted with hexane (750 mL). The mixture was cooled in ice for 1 h, then the brown solid was filtered off, washed with hexane, and dried under vacuum to afford the title compound (61.72 g, 73%).

Workup

  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. customto distil over
  6. additiondiluted with hexane (750 mL)
  7. temperatureThe mixture was cooled in ice for 1 h
  8. filtrationthe brown solid was filtered off
  9. washwashed with hexane
  10. customdried under vacuum

Sources & evidence

ORD record
ord-6df3bee89c804c4abd96b7726024bb4a
Source dataset
uspto-grants-2010_01
Patent number
US07648980B2

Reaction notes

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