4-Aminobenzyl alcohol → 3-Butyryl-4-(4-hydroxymethylphenylamino)-8-methoxyquinoline

HRID 1090629Notes

Reaction equation

HRID 1090629 reaction equation
[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][OH:25])=[CH:22][CH:21]=1>O1CCOCC1>[C:1]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[NH:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][OH:25])=[CH:22][CH:21]=1)=[CH:13][CH:12]=[CH:11][C:10]=2[O:17][CH3:18])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 693314-Aminobenzyl alcoholHCID 117775673-Butyryl-4-chloro-8-methoxyquinoline

Product 1

HCID 100892413-Butyryl-4-(4-hydroxymethylphenylamino)-8-methoxyquinolineYield 53.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-Butyryl-4-chloro-8-methoxyquinoline (2 g, 8 mmol), 4-aminobenzyl alcohol (2.3 g, I2 mmol) and 1,4-dioxan (50 ml) were heated at 70° for 1.5 hours, then more amine (0.9 g, 8 mmol) was added and heating continued for a further 6 hours. The solvent was evaporated and the product converted to free base. Recrystallisation from chloroform/ether gave 3-butyryl-4-(4-hydroxymethylphenylamino)-8-methoxyquinoline (1.5 g), m.p. 187°-189°.

Workup

  1. temperatureheating
  2. customThe solvent was evaporated
  3. customRecrystallisation from chloroform/ether

Sources & evidence

ORD record
ord-79b6b21825f54d1499b1bc89a42722a1
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

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