8-Amino-3-butyryl-4-(2-methylphenylamino)quinoline → 1-[8-(3-Morpholin-4-yl-propylamino)-4-o-tolylamino-quinolin-3-yl]-butan-1-one

HRID 1090673Notes

Reaction equation

HRID 1090673 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([C:12](=[O:16])[CH2:13][CH2:14][CH3:15])=[C:7]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24].Cl.Cl[CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>>[C:12]([C:8]1[CH:9]=[N:10][C:11]2[C:6]([C:7]=1[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH3:24])=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)(=[O:16])[CH2:13][CH2:14][CH3:15]

Participants

3

Reactant 2

HCID 102454028-Amino-3-butyryl-4-(2-methylphenylamino)quinolineHCID 122962834-(3-Chloropropyl)morpholinium chloride

Product 1

HCID 104562441-[8-(3-Morpholin-4-yl-propylamino)-4-o-tolylamino-quinolin-3-yl]-butan-1-oneYield 5%

Procedure

8-Amino-3-butyryl-4-(2-methylphenylamino)quinoline (6.5 g, 0.02 moles) and 3-chloropropylmorpholine hydrochloride (5.0 g, 0.025 moles) were heated together in fusion (150° C) for 20 minutes. The product was partitioned between ethyl acetate and dil. ammonia solution. The organic layer was washed twice with sodium dihydrogen phosphate solution (pH5), dried, filtered and evaporated. Chromatography (silica gel/chloroform/30-0% hexane) and crystallization from hexane gave 3-butyryl-4-(2-methyl phenylamino)-8-(3-morpholinopropylamino)quinoline as orange crystals (0.45 g, 5%), m.p. 110°-11° C.

Workup

  1. customThe product was partitioned between ethyl acetate and dil. ammonia solution
  2. washThe organic layer was washed twice with sodium dihydrogen phosphate solution (pH5)
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customChromatography (silica gel/chloroform/30-0% hexane) and crystallization from hexane

Sources & evidence

ORD record
ord-7a3a73d4bcba494eb07851d9de45ccc4
Source dataset
uspto-grants-1992_01
Patent number
US05082841

Reaction notes

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