HCID 19417643, compound → HCID 15817307, compound

HRID 865025Notes

Reaction equation

HRID 865025 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[C:6]([NH:14]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34]>[Ni].O1CCOCC1.CO>[NH2:14][C:6]1[C:7](=[O:13])[N:8]([CH3:12])[C:9]2[C:4]([C:5]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[Cl:34])=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

5

Reactant 1

HCID 19417643HCID 19417643, compound

Product 1

HCID 15817307HCID 15817307, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6-chloro-4-(2-chlorophenyl)-1,2-dihydro-1-methyl-3-(4-nitrobenzyloxycarbonylamino)-2-oxoquinoline (1.9 g, 3.8 mmol) and Raney nickel (1.9 g, 50% slurry in water) in 75 ml dioxane and 75 ml methanol was shaken under hydrogen (50 psi) in a Parr hydrogenation apparatus for 3 h. The catalyst was filtered and the filtrate was concentrated to dryness in vacuo. The residue was dissolved in 100 ml ethyl acetate and the solution was washed with 60 ml brine. The ethyl acetate solution was then dried (sodium sulfate) and concentrated in vacuo to a solid (1.2 g) which was purified by column chromatography on silica gel (150 g), eluting with 7:3 hexane/ethyl acetate to yield the title compound as an off-white solid (950 mg, 79% yield).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated to dryness in vacuo
  3. dissolutionThe residue was dissolved in 100 ml ethyl acetate
  4. washthe solution was washed with 60 ml brine
  5. dry with materialThe ethyl acetate solution was then dried (sodium sulfate)
  6. concentrationconcentrated in vacuo to a solid (1.2 g) which
  7. customwas purified by column chromatography on silica gel (150 g)
  8. washeluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-b80ae011e6f04033aec59b65be77cbbc
Source dataset
uspto-grants-1996_10
Patent number
US05565472

Reaction notes

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