HCID 178526754, compound → HCID 178507983, compound

HRID 2051480Notes

Reaction equation

HRID 2051480 reaction equation
[OH:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:10]([N+:18]([O-])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1>CO.O1CCCC1.[Pd]>[NH2:18][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([OH:1])[C:11]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

5

Reactant 1

HCID 178526754HCID 178526754, compound

Product 1

HCID 178507983HCID 178507983, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 2-hydroxy-3-morpholino-4-nitroquinoline (1.5 g, 0.0054 mol) was dissolved in a mixed solvent of methanol and tetrahydrofuran and subjected to catalytic reduction in the presence of 10g palladium-on-carbon. 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 was conducted to obtain 4-amino-2-hydroxy-3-morpholinoquinoline in an amount of 0.9 g (yield, 63%).

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

Sources & evidence

ORD record
ord-f5fab907a21c4e048c893d833d283663
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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