2-Methoxyaniline → HCID 21891184, compound

HRID 721598Notes

Reaction equation

HRID 721598 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]([OH:24])=O)=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.[CH3:50][O:51][C:52]1[C:53]([NH2:58])=[CH:54][CH:55]=[CH:56][CH:57]=1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[CH3:50][O:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[NH:58][C:22](=[O:24])[CH2:21][O:20][C:19]1[CH:25]=[CH:26][C:16]([O:15][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][CH:7]=2)=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 70002-MethoxyanilineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 21890558HCID 21890558, compound

Product 1

HCID 21891184HCID 21891184, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenoxy}acetic acid (150 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC.HCl) (122 mg), and 1-hydroxybenzotriazole hydrate (HOBT.H2O) (86 mg) were dissolved in chloroform (5 ml) to prepare a solution. o-Anisidine (63 mg) 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 (155 mg, yield 80%).

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-749b73019a954a96ba90b581eab13eb7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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