Diethyl Malonate → 7-Amino-4-hydroxy-1,8-naphthyridin-2(1H)-one

HRID 867257Notes

Reaction equation

HRID 867257 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.[C:9](OCC)(=[O:16])[CH2:10][C:11](OCC)=[O:12]>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH2:8][C:4]1[N:3]=[C:2]2[C:7]([C:9]([OH:16])=[CH:10][C:11](=[O:12])[NH:1]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 7761Diethyl MalonateHCID 88612,6-Diaminopyridine

Product 1

HCID 546804477-Amino-4-hydroxy-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

The procedure used was a modification of that by Lappin et al. [G. A. Lappin, Q. R. Petersen and C. E. Wheeler, J. Org. Chem. 15, 377 (1950)]. 2,6-Diaminopyridine (10.9 g, 0.1 mole) and 16.0 g (0.1 mole) of diethyl malonate in 250 ml of diphenyl ether were heated with stirring under an air condenser at 170°-180° for 1 hr. Then the temperature was slowly increased to 245°. The total heating time from room temperature to final temperature was 4.5 hr. Off-white solid began to separate soon after 180° was reached. The slurry was cooled, diluted with 100 ml of benzene, filtered, and the solid product washed several times with benzene; 17.7 g (100%) after drying. The experiment was also readily performed on a 0.4-mole scale.

Workup

  1. temperatureThen the temperature was slowly increased to 245°
  2. waitThe total heating time from room temperature to final temperature was 4.5 hr
  3. customto separate soon after 180°
  4. temperatureThe slurry was cooled
  5. additiondiluted with 100 ml of benzene
  6. filtrationfiltered
  7. washthe solid product washed several times with benzene
  8. custom17.7 g (100%) after drying

Sources & evidence

ORD record
ord-c682cb9ea9b54c60ae038da12625c6ee
Source dataset
uspto-grants-1978_07
Patent number
US04103257

Reaction notes

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