HCID 19771712, compound → HCID 19771742, compound

HRID 1614589Notes

Reaction equation

HRID 1614589 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]2[C:10]([C:11](=[O:13])[CH:12]=1)=[N:9][C:8](OC)=[CH:7][CH:6]=2)[CH3:2].[H][H]>C(O)(=O)C.[Pt]=O>[CH2:1]([C:3]1[NH:4][C:5]2[CH2:6][CH2:7][CH2:8][NH:9][C:10]=2[C:11](=[O:13])[CH:12]=1)[CH3:2]

Participants

5

Reactant 2

HCID 19771712HCID 19771712, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19771742HCID 19771742, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Compound E5 (5.0 g) was dissolved in glacial acetic acid (50 ml) and catalytically hydrogenated at atmospheric pressure over platinum oxide (0.5 g). When hydrogen uptake ceased, the catalyst was removed by filtration through diatomaceous earth. The solvent was removed by evaporation and the residue purified by flash chromatography eluting with ethyl acetate/methanol/aqueous ammonia (17:2:1 v/v), to give 2-ethyl-5,6,7,8-tetrahydro-1,5-naphthyridin-4(1H)-one (D5) (3.2 g), m.p. 206°-209° C. (after trituration with ethyl acetate); NMR (d6 -DMSO): 1.15(t,3H), 1.7-1.9(m,2H), 2.35(q,2H), 2.55(t,2H), 3.1(t,2H), 5.75(s,1H), 10.6-11.1(br s,1H).

Workup

  1. customthe catalyst was removed by filtration through diatomaceous earth
  2. customThe solvent was removed by evaporation
  3. customthe residue purified by flash chromatography
  4. washeluting with ethyl acetate/methanol/aqueous ammonia (17:2:1 v/v)

Sources & evidence

ORD record
ord-c45197d9077a4e43b8ec5f84d7e1aa84
Source dataset
uspto-grants-1993_03
Patent number
US05198434

Reaction notes

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