Water → HCID 19771712, compound

HRID 893620Notes

Reaction equation

HRID 893620 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 mixture 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-naphthyridine-4 (1H)-one (B4) (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 mixture 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-b5e79942028b4776992b1c10ec1d951e
Source dataset
uspto-grants-1992_06
Patent number
US05126344

Reaction notes

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