2,4-Difluoroaniline → HCID 9957468, compound

HRID 1375808Notes

Reaction equation

HRID 1375808 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:22]=[CH:21][C:19]([NH2:20])=[C:18]([N+:23]([O-:25])=[O:24])[CH:17]=1.ClC(Cl)(O[C:30](=[O:36])OC(Cl)(Cl)Cl)Cl.[F:38][C:39]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:40]=1[NH2:41].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[F:38][C:39]1[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:40]=1[NH:41][C:30]([NH:20][C:19]1[CH:21]=[CH:22][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][C:18]=1[N+:23]([O-:25])=[O:24])=[O:36]

Participants

7

Reactant 4

HCID 97092,4-DifluoroanilineHCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 218907304-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline

Product 1

HCID 9957468HCID 9957468, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-nitroaniline (100 mg) was dissolved in chloroform (10 ml) and triethylamine (1 ml), and a solution of triphosgene (96 mg) in chloroform was then added to the solution. The mixture was heated under reflux for 5 min. Next, 2,4-difluoroaniline (45 mg) was added to the reaction solution, and the mixture was further heated under reflux overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was supported on diatomaceous earth, followed by extraction with chloroform. The solvent was removed by distillation under the reduced pressure. The residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (3/1) to give 81 mg (yield 56%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 min
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux overnight
  5. extractionfollowed by extraction with chloroform
  6. customThe solvent was removed by distillation under the reduced pressure
  7. customThe residue was purified by thin-layer chromatography on silica gel by development with chloroform/acetone (3/1)

Sources & evidence

ORD record
ord-63af8208d79c409b8417dcef485533f8
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

Loading…