3,4,5-Trimethoxybenzoic Acid → 4-(2-Chlorophenyl)-6,8-dimethyl-3-[3-(3,4,5-trimethoxyphenyl)ureido]-quinoline

HRID 1656425Notes

Reaction equation

HRID 1656425 reaction equation
COC1C=C(C=C(OC)C=1OC)C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:33][O:34][C:35]1[CH:36]=[C:37]([N:45]=[C:46]=[O:47])[CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42].[NH2:48][C:49]1[CH:50]=[N:51][C:52]2[C:57]([C:58]=1[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][C:60]=1[Cl:65])=[CH:56][C:55]([CH3:66])=[CH:54][C:53]=2[CH3:67]>O1CCOCC1.C(N(CC)CC)C>[Cl:65][C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][C:59]=1[C:58]1[C:57]2[C:52](=[C:53]([CH3:67])[CH:54]=[C:55]([CH3:66])[CH:56]=2)[N:51]=[CH:50][C:49]=1[NH:48][C:46]([NH:45][C:37]1[CH:36]=[C:35]([O:34][CH3:33])[C:40]([O:41][CH3:42])=[C:39]([O:43][CH3:44])[CH:38]=1)=[O:47]

Participants

7

Reactant 4

HCID 83573,4,5-Trimethoxybenzoic AcidHCID 199401P,P-Diphenylphosphinic azideHCID 5177665-Isocyanato-1,2,3-trimethoxybenzeneHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

Product 1

HCID 150351544-(2-Chlorophenyl)-6,8-dimethyl-3-[3-(3,4,5-trimethoxyphenyl)ureido]-quinoline

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (0.37 ml) was added dropwise to a mixture of 3,4,5-trimethoxybenzoic acid (563 mg), diphenylphosphoryl azide (730 mg) and dioxane (10 ml) under stirring. The mixture was further stirred for 30 mins. at room temperature and then for 40 mins. under reflux to prepare a solution of 3,4,5-trimethoxyphenyl isocyanate. After cooling, to the resultant solution was added 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (500 mg), and the whole was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was purified by a column chromatography on silica gel and recrystallized from dichloromethane to give 4-(2-chlorophenyl)-6,8-dimethyl-3-[3-(3,4,5-trimethoxyphenyl)ureido]-quinoline as colorless needles. Yield 490 mg (56.3%). m.p. 204°-206° C.

Workup

  1. stirringThe mixture was further stirred for 30 mins
  2. temperatureunder reflux
  3. stirringthe whole was stirred at room temperature overnight
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by a column chromatography on silica gel
  6. customrecrystallized from dichloromethane

Sources & evidence

ORD record
ord-146ebc2f9cf64daab74b10f882d13b48
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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