HCID 178418361, compound → HCID 178469661, compound

HRID 1168492Notes

Reaction equation

HRID 1168492 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([N+:19]([O-])=O)[CH:8]=[C:9]([CH2:12][N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].[H][H]>CN(C=O)C.[Pd]>[NH2:19][C:7]1[CH:8]=[C:9]([CH2:12][N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][C:3]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:2]2[OH:1]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178469669HCID 178469669, compound

Product 1

HCID 178469661HCID 178469661, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 4-hydroxy-6-(4-morpholinylmethyl)-8-nitro-3-quinolinecarboxylate (Preparation 1, 1.36 g) in DMF (50 mL) is hydrogenated at 50 psi hydrogen pressure in the presence of 10% Pd/C (400 mg) for 15 min. The catalyst is filtered off and the filtrate is evaporated. The residual solid is triturated with methanol to afford 1.12 g of the title compound. Physical characteristics. 1H NMR (DMSO-d6) δ1.28, 2.35, 3.44, 3.57, 4.21, 5.59, 6.98, 7.33, 8.41.

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. customThe residual solid is triturated with methanol

Sources & evidence

ORD record
ord-14c893af90f74779bec835aadaa35786
Source dataset
uspto-grants-2003_09
Patent number
US06624159B2

Reaction notes

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