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

HRID 638974Notes

Reaction equation

HRID 638974 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 portionwise 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 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%).

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 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

Sources & evidence

ORD record
ord-4286c904dd854382b08f8ccacb54f1fc
Source dataset
uspto-grants-2010_04
Patent number
US07691850B2

Reaction notes

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