p-Toluenesulfonic acid → HCID 178432093, compound

HRID 1357488Notes

Reaction equation

HRID 1357488 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]([CH:11]([C:17]([CH3:19])=O)[C:12](OCC)=[O:13])([CH3:10])[CH3:9].C(Cl)(Cl)Cl.C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[OH:13][C:12]1[C:7]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:1]=[C:17]([CH3:19])[C:11]=1[CH:8]([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 6115AnilineHCID 6212ChloroformHCID 95544Butanoic acid, 2-acetyl-3-methyl-, ethyl ester

Product 1

HCID 178432093HCID 178432093, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4.56 ml (50 mmol) of aniline and 10.7 ml (60 mmol) of ethyl 2-isopropylacetoacetate were mixed with 50 ml of chloroform. 0.48 g (2.5 mmol) of para-toluenesulfonic acid was added, and the reaction mixture was refluxed with continuous removal of the water produced in the reaction. After 2 d chloroform was removed in vacuum, and the residue was refluxed in 10 ml of phenyl ether. After cooling, the precipitate was filtered and washed with diethyl ether to give 4-hydroxy-3-isopropyl-2-methylquinoline (21%). Following the procedure of Step 3 in Example 1, but substituting 4-hydroxy-3-isopropyl-2-methylquinoline for 9-(10H)acridone, 4-chloro-3-isopropyl-2-methylquinoline (100%) was obtained, which was reacted with 4-(4-methylpiperazin-1-yl)aniline (following the procedure of Step 4 in Example 1), to afford the title compound with 61% yield (overall yield 13%).

Workup

  1. customproduced in the reaction
  2. customAfter 2 d chloroform was removed in vacuum
  3. temperaturethe residue was refluxed in 10 ml of phenyl ether
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1c2d47777612497eb73d507bc1099956
Source dataset
uspto-grants-2003_07
Patent number
US06593324B2

Reaction notes

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