HCID 14986013, compound → HCID 14986014, compound

HRID 2051474Notes

Reaction equation

HRID 2051474 reaction equation
[NH:1]([C:8]1[C:17]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:16]([N+:24]([O-])=O)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.[Pd]>[NH2:24][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:17]=1[N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

Participants

4

Reactant 1

HCID 14986013HCID 14986013, compound

Product 1

HCID 14986014HCID 14986014, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 2-anilino-3-morpholino-4-nitroquinoline (2.9 g, 0.0083 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 methanol was conducted to obtain 4-amino-2-anilino-3-morpholinoquinoline in an amount of 1.89 g (yield, 69%).

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 methanol

Sources & evidence

ORD record
ord-04db4d0b6f5b4493bc0a8c252d8c6dd9
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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