HCID 178418361, compound → HCID 178469660, compound

HRID 2119330Notes

Reaction equation

HRID 2119330 reaction equation
[CH2:1]([N:8](C)[C:9]1[CH:10]=[C:11]([CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][C:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:14]2[OH:24])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[OH:24][C:14]1[C:13]2[C:18](=[C:9]([NH:8][CH3:1])[CH:10]=[C:11]([CH2:25][N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:12]=2)[N:17]=[CH:16][C:15]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178469657HCID 178469657, compound

Product 1

HCID 178469660HCID 178469660, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 8-[benzyl(methyl)amino]4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxylate (500 mg, 1.15 mmol), 10% palladium charcoal (0.25 g) in ethanol (100 mL) is hydrogenated (50 psi initial hydrogen pressure) until HPLC shows that all the starting material has been reduced (2.5 h). The solution is filtered, the solvent removed, and the residual oil is applied in chloroform to a silica gel column which is eluted with 5-10% methanol/chloroform. After elution of a small amount of ethyl 4-hydroxy-8-(methylamino)-6-methyl-3-quinolinecarboxylate, the title compound (280 mg) is obtained.

Workup

  1. custom(2.5 h)
  2. filtrationThe solution is filtered
  3. customthe solvent removed
  4. washis eluted with 5-10% methanol/chloroform
  5. washAfter elution of a small amount of ethyl 4-hydroxy-8-(methylamino)-6-methyl-3-quinolinecarboxylate

Sources & evidence

ORD record
ord-cec8f155d0f24ac7885344db26dde03e
Source dataset
uspto-grants-2004_02
Patent number
US06686356B2

Reaction notes

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