HCID 14423306, compound → HCID 15135971, compound

HRID 893834Notes

Reaction equation

HRID 893834 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:24]2[C:8]3[N:9]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:10]4[C:15]([C:16](=[O:17])[C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1)=[CH:14][CH:13]=[CH:12][N:11]=4.[H][H]>[Pd].C(O)C>[OH:1][C:2]1[CH:26]=[CH:25][C:24]2[C:8]3[N:9]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:10]4[NH:11][CH2:12][CH2:13][CH2:14][C:15]=4[C:16](=[O:17])[C:7]=3[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 14423306HCID 14423306, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15135971HCID 15135971, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Charge a Paar bottle with 5,6-dihydro-3-hydroxy-12-phenyl-naphtho[1,2-b] [1,8]naphthyridin-7(12H)-one, an equal weight of 5% Pd on carbon, and ethanol. Pressurize the bottle with hydrogen to about 50 psi, and shake the contents in a Paar apparatus at 25° C. Monitor the progress of hydrogenation by pressure changes or by thin-layer chromatography. When hydrogen uptake ceases, remove catalyst by filtration and ethanol by evaporation. Crystallize the residue to obtain 5,6,8,9,10,11-hexahydro-3-hydroxy-12-phenyl-naphtho[1,2-b] [1,8]naphthyridin-7(12H)-one, m.p. >330° C. after crystallization from C2H5OH.

Workup

  1. customat 25° C
  2. customremove catalyst
  3. filtrationby filtration and ethanol
  4. customby evaporation
  5. customCrystallize the residue

Sources & evidence

ORD record
ord-5722c2240cc743219d2943445908dbab
Source dataset
uspto-grants-1992_06
Patent number
US05126352

Reaction notes

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