Methyl 2-anilinopyridine-3-carboxylate → 4-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 1248945Notes

Reaction equation

HRID 1248945 reaction equation
[C:1]1([NH:7][C:8]2[C:13]([C:14]([O:16]C)=O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][C:19](C)([O-:21])C.[K+]>C(OCCCC)(=O)C>[OH:16][C:14]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:19](=[O:21])[CH:18]=1

Participants

4

Reactant 2

HCID 10998755Methyl 2-anilinopyridine-3-carboxylateHCID 23665647Potassium tert-butoxide2×

Product 1

HCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 31272Butyl AcetateSolvent2×

Procedure

To a stirred solution of 1 kg. of methyl 2-phenylamino-3-pyridine carboxylate in 3.97 liters of n-butyl acetate there is added portionwise, 1.1 kg. of potassium tertiary butoxide. After the addition of the potassium tertiary butoxide, there is added an additional 1.32 liters of n-butyl acetate. The reaction mixture is heated to reflux for 20 hours during which the internal temperature of the reaction mixture rose from 90° C. to 122° C. During this period, 1.8 liters of liquid is removed from the reaction mixture via a Dean-Stark trap. Xylene (3.0 liters) is added to the reaction mixture and the remainder of the n-butyl acetate is removed via the Dean-Stark trap. The reaction mixture is cooled and the potassium salt is collected by filtration, washed with toluene and air dried. The crude potassium salt is dissolved in 12 liters of water, the aqueous solution is extracted with toluene, acidified to pH 2 and the product filtered and dried; weight 937 g., m.p. 311°-313° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 20 hours during which the internal temperature of the reaction mixture
  3. customrose from 90° C. to 122° C
  4. waitDuring this period
  5. custom1.8 liters of liquid is removed from the reaction mixture via a Dean-Stark trap
  6. additionXylene (3.0 liters) is added to the reaction mixture
  7. customthe remainder of the n-butyl acetate is removed via the Dean-Stark trap
  8. temperatureThe reaction mixture is cooled
  9. filtrationthe potassium salt is collected by filtration
  10. washwashed with toluene and air
  11. customdried
  12. dissolutionThe crude potassium salt is dissolved in 12 liters of water
  13. extractionthe aqueous solution is extracted with toluene
  14. filtrationthe product filtered
  15. customdried

Sources & evidence

ORD record
ord-cbadae9c3c8e45d7ab4f90ed19bccd23
Source dataset
uspto-grants-1986_12
Patent number
US04628055

Reaction notes

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