HCID 66703966, compound → HCID 24810534, compound

HRID 425265Notes

Reaction equation

HRID 425265 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=3)[N:11]=[C:10]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH:9]=2)=[CH:4][CH:3]=1>O.C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=3)[N:11]=[C:10]([N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66703966HCID 66703966, compound

Product 1

HCID 24810534HCID 24810534, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

5.49 g of sodium/mercury amalgam were added over the course of 5 hours to a solution of 250 mg of 4-(4-aminophenyl)-6-chloro-2-diethylaminoquinoline in 2.5 ml of water and 16 ml of ethanol while stirring. The mixture was stirred overnight and decanted to remove the Hg precipitate, and the solvent was distilled under reduced pressure. The residue was mixed with water and extracted with ethyl acetate. The solid product as pale residue was dissolved in a little ethyl acetate, acidified with ethereal HCl, stirred at room temperature and filtered with suction.

Workup

  1. stirringThe mixture was stirred overnight
  2. customdecanted
  3. customto remove the Hg precipitate
  4. distillationthe solvent was distilled under reduced pressure
  5. additionThe residue was mixed with water
  6. extractionextracted with ethyl acetate
  7. dissolutionThe solid product as pale residue was dissolved in a little ethyl acetate
  8. stirringstirred at room temperature
  9. filtrationfiltered with suction

Sources & evidence

ORD record
ord-0cff8a8bda9f48c39d01580b84a1c4ae
Source dataset
uspto-grants-2012_01
Patent number
US08106204B2

Reaction notes

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