Water → HCID 19771712, compound

HRID 1614588Notes

Reaction equation

HRID 1614588 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[C:10]([CH2:14][C:15](OC)=[O:16])(=O)[CH2:11][CH3:12].O>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:11]([C:10]1[NH:1][C:2]2[C:7]([C:15](=[O:16])[CH:14]=1)=[N:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)[CH3:12]

Participants

6

Reactant 3

HCID 962WaterHCID 811216-Methoxy-3-pyridinylamineHCID 121699Methyl 3-oxovalerate

Product 1

HCID 19771712HCID 19771712, compoundYield 39.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 5-amino-2-methoxypyridine (50 g), methyl propionylacetate (57.3 g) and p-toluenesulphonic acid (0.5 g) in benzene (200 ml) was heated under reflux with azeotropic removal of water for 20 hours. Volatile material was removed by evaporation and the residue added to a refluxing eutectic mixure of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (140 ml). The solution was heated under reflux for 1 hour, cooled and diluted with hexane (500 ml). The precipitated solid was filtered off and triturated with hot methanol (500 ml) to give 2-ethyl-6-methoxy-1,5-naphthyridin-4(1H)-one (E5) (32.3 g), as a pale brown solid, m.p. 279°-281° C.; NMR (d6 -DMSO): 1.2(t,3H), 2.65(q,2H), 3.95(s,3H), 6.3(br s, 1H), 7.15(d,1H), 7.95(d,1H).

Workup

  1. customVolatile material was removed by evaporation
  2. additionthe residue added to a refluxing eutectic mixure of 26.5% v/v diphenyl and 73.5% v/v diphenyl oxide (140 ml)
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 1 hour
  5. temperaturecooled
  6. additiondiluted with hexane (500 ml)
  7. filtrationThe precipitated solid was filtered off
  8. customtriturated with hot methanol (500 ml)

Sources & evidence

ORD record
ord-f9dcca519ef5498db071dd9bf5fca534
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

Loading…