Stannous Chloride → 1-[4-(8-Aminoquinolin-4-yloxy)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)urea

HRID 554482Notes

Reaction equation

HRID 554482 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=2)=[O:23])=[CH:17][CH:16]=1)([O-])=O.[Sn](Cl)Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[C:9]2[O:14][C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=2)=[O:23])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 595094071-[4-(8-Nitroquinolin-4-yloxy)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)urea

Product 1

HCID 445836041-[4-(8-Aminoquinolin-4-yloxy)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)ureaYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-[4-(8-Nitroquinolin-4-yloxy)phenyl]-3-(4-chloro-3-trifluoromethylphenyl)urea (12.0 mg, 0.027 mmol) and tin (II) chloride (25.9 mg, 0.11 mmol) were dissolved in ethanol (0.23 mL), and then refluxed with stirring for 30 minutes. When the reaction was completed, the solvent was removed by vacuum distillation, the resultant was extracted with ethyl acetate and saturated sodium bicarbonate. Combined organic layers were dried with anhydrous sodium sulfate, and then filtered. The solvent was removed and then filtered a brown solid product to obtain 8.1 mg of the desired compound (yield 75.0%).

Workup

  1. temperaturerefluxed
  2. customthe solvent was removed by vacuum distillation
  3. extractionthe resultant was extracted with ethyl acetate and saturated sodium bicarbonate
  4. dry with materialCombined organic layers were dried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed
  7. filtrationfiltered a brown solid product

Sources & evidence

ORD record
ord-4ff55052840c4c65818d5c0892302df5
Source dataset
uspto-grants-2011_11
Patent number
US08049014B2

Reaction notes

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