p-Toluidine → HCID 21890345, compound

HRID 721608Notes

Reaction equation

HRID 721608 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:26]=[CH:25][C:19]([O:20][CH2:21][C:22](O)=[O:23])=[CH:18][CH:17]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH2:49][C:50]1[CH:55]=[CH:54][C:53]([CH3:56])=[CH:52][CH:51]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.O>[CH3:56][C:53]1[CH:54]=[CH:55][C:50]([NH:49][C:22](=[O:23])[CH2:21][O:20][C:19]2[CH:25]=[CH:26][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:17][CH:18]=2)=[CH:51][CH:52]=1

Participants

8

Reactant 5

HCID 7813p-ToluidineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21890558HCID 21890558, compound

Product 1

HCID 21890345HCID 21890345, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

2-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenoxy}acetic acid (150 mg), WSC.HCl (122 mg), and HOBT.H2O (86 mg) were dissolved in chloroform (5 ml) to prepare a solution. p-Toluidine (0.055 ml) was then added to the solution, and the mixture was heated under reflux for 3 hr. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with 1 N hydrochloric acid, water, and saturated brine and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography using chloroform/methanol for development to give the title compound (76 mg, yield 41%).

Workup

  1. customto prepare a solution
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hr
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with 1 N hydrochloric acid, water, and saturated brine
  6. dry with materialwas then dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under the reduced pressure
  8. customThe residue was purified by thin-layer chromatography

Sources & evidence

ORD record
ord-9101d514aceb49279065c6e87aa4cf9f
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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