Water → HCID 19756351, compound

HRID 1587830Notes

Reaction equation

HRID 1587830 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6][CH:7]=1.[C:29]([CH2:33][C:34](OC)=[O:35])(=O)[CH2:30][CH3:31].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1C=CC=CC=1>[Si:12]([O:11][CH2:10][CH2:9][O:8][C:5]1[N:6]=[C:7]2[C:2](=[CH:3][CH:4]=1)[NH:1][C:29]([CH2:30][CH3:31])=[CH:33][C:34]2=[O:35])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 121699Methyl 3-oxovalerateHCID 19756412HCID 19756412, compound

Product 1

HCID 19756351HCID 19756351, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of compound C (10 g), methyl propionylacetate (11.5 g) and p-toluenesulphonic acid (0.1 g) in benzene (40 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 (30 ml). The solution was heated under reflux for 1 hour, cooled and diluted with hexane (100 ml). The precipitated solid was filtered off and triturated with hot methanol (100 ml) to give 2-ethyl-6-[2-(trimethylsilyl)ethoxy]-1,5-naphthyridin-4-(1H)-one (D) (in 62% yield) as a white solid, m.p. 193° C.; NMR: -0.1(s,9H), 0.85(t,2H), 1.3(t,3H), 2.8(q,2H), 4.1(t,2H), 6.55(s,1H), 6.9(d,1H), 8.2(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 (30 ml)
  3. temperatureThe solution was heated
  4. temperatureunder reflux for 1 hour
  5. temperaturecooled
  6. additiondiluted with hexane (100 ml)
  7. filtrationThe precipitated solid was filtered off
  8. customtriturated with hot methanol (100 ml)

Sources & evidence

ORD record
ord-5b75ffbc2bad442695fc930bfec7e133
Source dataset
uspto-grants-1993_06
Patent number
US05219863

Reaction notes

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