Water → 6-Methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinoline

HRID 2290653Notes

Reaction equation

HRID 2290653 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:24][CH3:25])[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12].[C:26]1(=O)[O:31][C:29](=[O:30])[C:28]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]12.O>C1(C)C(C)=CC=CC=1>[CH3:25][O:24][C:4]1[C:5]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:21])([F:22])[F:23])[CH:15]=2)=[C:6]2[C:11](=[C:2]([N:1]3[C:29](=[O:30])[C:28]4=[CH:32][CH:33]=[CH:34][CH:35]=[C:27]4[C:26]3=[O:31])[CH:3]=1)[N:10]=[CH:9][CH:8]=[C:7]2[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 6811Phthalic AnhydrideHCID 130042034-Methyl-5-(3-trifluoromethylphenoxy)-6-methoxy-8-aminoquinoline

Product 1

HCID 137459246-Methoxy-4-methyl-8-phthalimido-5-(3-trifluoromethylphenoxy)quinolineYield 100%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline (I) (6.96 g, 20 mmol) and phthalic anhydride (3.25 g, 22 mmol) in xylene (100 mL) was refluxed with water removal via a Dean-Stark trap for 24 hours. After cooling, filtration gave 9.5 g (100%) of the title compound, mp 228°-30° C. Recrystallization from ethanol raised the mp to 228°-31° C.

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration

Sources & evidence

ORD record
ord-71695aed5bdf41778ed1d0ce5745a144
Source dataset
uspto-grants-1986_10
Patent number
US04617394

Reaction notes

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