HCID 14986019, compound → HCID 14986020, compound

HRID 2051477Notes

Reaction equation

HRID 2051477 reaction equation
[CH2:1]([O:3][C:4]1[C:13]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[C:12]([N+:20]([O-])=O)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:2]>O1CCCC1.[Pd]>[NH2:20][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([O:3][CH2:1][CH3:2])[C:13]=1[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 1

HCID 14986019HCID 14986019, compound

Product 1

HCID 14986020HCID 14986020, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 2-ethoxy-3-morpholino-4-nitroquinoline (1.2 g, 0.004 mol) was dissolved in tetrahydrofuran (10 ml) and subjected to reduction in the presence of 10g palladium-on-carbon (0.3 g). After completion of the reaction, the palladium-on-carbon catalyst was filtered off and the mother liquor was concentrated. Following purification by chromatography on an alumina column using chloroform as a developing solvent, recrystallization from chloroform gas performed to obtain 4-amino-2-ethoxy-3-morpholinoquinoline in an amount of 0.7 g (yield, 60%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe palladium-on-carbon catalyst was filtered off
  3. concentrationthe mother liquor was concentrated
  4. custompurification by chromatography on an alumina column
  5. customas a developing solvent, recrystallization from chloroform gas

Sources & evidence

ORD record
ord-3a9b3fb36a67490c8fb97200b837fa89
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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